No renderable structure data available
ClC1C=C(C(=CC=1Cl)N)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3,4-Dichloro-6-fluoroaniline |
|---|---|
| IUPAC Name | — |
| CAS Number | 2729-36-4 |
| Database ID | 223091 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3,4-Dichloro-6-fluoroaniline (CAS 2729-36-4) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 223091
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-47d3f845b251409cb4a8de471c6fe9a4Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-04e88fef105846f19664e349a610999eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e8d483861a77405a9ab933ea1a1e19acConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3,4-Dichloro-6-fluoroaniline (1 equivalent) was reacted with 4-chloro-6-nitroquinazoline (3.5 equivalents), in iso-propylalcohol. After filtration, 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-nitroquinazoline (compound 1) was obtained in 78% yield. After filtration
Source ID: ord-4a4f25d577154b809f69c5e6408ff8e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In one particular, 3,4-dichloro-6-fluoroaniline is reacted with 4-chloro-6-nitroquinazoline, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-nitroquinazoline, which is reduced, by means of an ethanolic solution of hydrazine hydrate and Raney®Nickel, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-aminoquinazoline. Then, the 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-aminoquinazoline is reacted with a carbon-11 labeled acryloyl chloride so as to produce a carbon-11 labeled {4-[(3,4-dichloro-6-fluorophenyl)amino]quinazoline-6-yl]acrylamide (radiolabeled Compound 3).
Source ID: ord-01f954d9b7ed424a880d8c81650992e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3,4-Dichloro-6-fluoroaniline (1 equivalent) was reacted with 4-chloro-7-fluoro-6-nitroquinazoline (3.5 equivalents), in iso-propylalcohol. After filtration, 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline was obtained in 78% yield. After filtration
Source ID: ord-1042ad855505453485b72441af00c3aeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3,4-Dichloro-6-fluoroaniline (1 equivalent, prepared as described in U.S. Pat. No. 6,126,917) was reacted with 4-chloro-6-nitroquinazoline (3.5 equivalents, prepared by reacting 6-nitroquinazoline with thionyl chloride, according to known procedures), in iso-propylalcohol. After filtration, 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-nitroquinazoline (compound 1) was obtained in 60% yield. m.p.=270–271° C.; MS (m/z): 353.2, 355.2 (M+); 1H-NMR: δ=6.97 (d, 1H), 7.345 (d, 1H), 7.885 (d, 1H), 8.405 (d, 1H), 8.554 (dd, 1H), 8.8 (d, 1H) ppm. HPLC conditions: C-18 column, 55% acetate buffer, PH=3.8/45% acetonitrile, flow=1 ml/min; r.t.=7.15 minutes. After filtration
Source ID: ord-83e5d3a1fcd541d29990cc006885a035Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In one particular, 3,4-dichloro-6-fluoroaniline is reacted with 4-chloro-6-nitroquinazoline, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-nitroquinazoline, which is reduced, by means of an ethanolic solution of hydrazine hydrate and Raney®Nickel, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-aminoquinazoline. Then, the 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-aminoquinazoline is reacted with 4-bromocrotonyl chloride, so as to produce 4-bromo-N-{4-[(3,4-dichloro-6-fluorophenyl)amino]quinazoline-6-yl}-2-butenamide, which is then reacted with methylamine, so as to produce N-{4-[(3,4-dichloro-6-fluorophenyl)amino]quinazoline-6-yl}-4-(methylamino)-2-butenamide. The obtained methylamino derivative of the butenamide is reacted with a carbon-11 labeled methyliodide, so as to produce a carbon-11 labeled N-{4-[(3,4-dichloro-6-fluorophenyl)amino]quinazoline-6-yl}-4-(dimethylamino)-2-butenamide (carbon-11 labeled Compound 4).
Source ID: ord-bfff5b6aa96840d1911371df5d83a26cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In another particular, which includes a quinazoline that is substituted by two different reactive groups at positions 6 and 7 thereof, 3,4-dichloro-6-fluoroaniline is reacted with 4-chloro-7-fluoro-6-nitroquinazoline, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline. The 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline is then reacted with a sodium salt of 3-(4-morpholinyl-1-propanol), so as to produce 4-[(3,4-dichloro-6-fluoro-phenyl)amino]-7-[3-(4-morpholinyl)propoxy]-6-nitroquinazoline, which is reduced, by means of an ethanolic solution of hydrazine hydrate and Raney®Nickel, so as to produce 6-amino-4-[(3,4-dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]quinazoline. The product is then reacted with a carbon-11 labeled acryloyl chloride so as to produce a carbon-11 labeled N-{4-[(3,4-dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]quinazoline-6-yl}acrylamide (carbon-11 labeled morpholino-substituted Compound 3).
Source ID: ord-66fb621122b84a2b986c4ce07a4fd5a3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In one particular, which includes a quinazoline that is substituted by one reactive group at position 6 thereof, 3,4-dichloro-6-fluoroaniline is reacted with 4-chloro-6-nitroquinazoline, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-nitroquinazoline, which is reduced, by means of an ethanolic solution of hydrazine hydrate and Raney®Nickel, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-aminoquinazoline. Then, the 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-aminoquinazoline is reacted with a carbon-11 labeled acryloyl chloride so as to produce a carbon-11 labeled N-{4-[(3,4-dichloro-6-fluorophenyl)amino]quinazoline-6-yl}acrylamide (carbon-11 labeled Compound 3).
Source ID: ord-5370d7db4ff949b28a752734447fc010Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Tin (II) chloride dehydrate (27.0 g, 119.6 mmol) was dissolved in ethanol and 1,2-dichloro-4-fluoro-5-nitrobenzene (5.0 g, 23.8 mmol) was added dropwise. Temperature rose to near reflux during the addition and was complete upon cooling. The reaction mixture was carefully added to saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. The organic phase was washed several more times with water, dried, filtered and concentrated to give the title compound as a yellow solid: 1H NMR (CDCl3): δ 7.17 (d, 1H), 6.84 (d, 1H), 3.78 (br s, 2H). to near reflux during the addition upon cooling extracted with ethyl acetate The organic phase was washed several more times with water dried filtered concentrated
Source ID: ord-c25086f663c14426b499312ee75a4528Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Tin (II) chloride dehydrate (27.0 g, 119.6 mmol) was dissolved in ethanol and 1,2-dichloro-4-fluoro-5-nitrobenzene (5.0 g, 23.8 mmol) was added dropwise. Temperature rose to near reflux during the addition and was complete upon cooling. The reaction mixture was carefully added to saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. The organic phase was washed several more times with water, dried, filtered and concentrated to give the title compound as a yellow solid: 1H NMR (CDCl3): δ 7.17 (d, 1H), 6.84 (d, 1H), 3.78 (br s, 2H). to near reflux during the addition upon cooling extracted with ethyl acetate The organic phase was washed several more times with water dried filtered concentrated
Source ID: ord-c25086f663c14426b499312ee75a4528PubChem References
These sources are listed in the compound's public database record.
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