Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate → 3-(4-Amino-3-Fluoro-phenyl)-isoxazole-5-carboxylic acid ethyl ester

HRID 75795

Reaction equation

HRID 75795 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([F:20])[CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].C(OC(C1ON=C(C2C=CC(N)=CC=2)C=1)=O)C>>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([F:20])[CH:12]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 53407704Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylateHCID 673525333-(3-Fluoro-4-nitro-phenyl)-isoxazole-5-carboxylic acid ethyl ester

Product 1

HCID 673526613-(4-Amino-3-Fluoro-phenyl)-isoxazole-5-carboxylic acid ethyl esterYield 55%

Procedure

The title compound was prepared from 3-(3-fluoro-4-nitro-phenyl)-isoxazole-5-carboxylic acid ethyl ester by following the procedure as described for the preparation of 3-(4-Amino-phenyl)-isoxazol-5-carboxylic acid ethyl ester (Example 1, Step 2) in 55% yield; MS (m/z): 250; 1H NMR (DMSO-d6) δ: 1.31 (t, 3H, CH2CH3), 4.36 (q, 2H, CH2CH3), 5.7 (s, 2H, NH2), 6.81 (t, 1H), 7.48 (d, 1H, J=9.0), 7.56 (d, 1H), 7.74 (s, 1H, 4-H).

Sources & evidence

ORD record
ord-70dd4ddd7cfa4db1a60d4bf918efe399
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

Loading…