HCID 22025639, compound → HCID 22025674, compound

HRID 2181459Notes

Reaction equation

HRID 2181459 reaction equation
[F:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][C:15]=2[F:23])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7]C)=[O:6]>CCO>[F:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][C:15]=2[F:23])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 22025639HCID 22025639, compound

Product 1

HCID 22025674HCID 22025674, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3,4-difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]benzoate was deprotected using EtOH/1 M NaOH as above to afford 3,4-difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]benzoic acid as a crystalline cream solid (93%); m.p. (EtOAc/hexane) 196-200° C. 1H NMR [400 MHz, (CD3)2SO] δ 13.67 (v br s, 1 H), 9.28 (br s, 1 H), 7.80 (ddd, J=8.4, 6.1, 1.8 Hz, 1 H), 7.13-6.93 (m, 4 H), 4.65 (br s, 1 H), 3.63-3.55 (br m, 2 H), 2.69 (t, J=6.8 Hz, 2 H). Anal. calcd. for C15H12F3NO3: C, 57.9; H, 3.9; N, 4.5. Found C, 58.3; H, 4.1; N, 4.7.

Sources & evidence

ORD record
ord-35e1e2fcfe7b445984f33a3973e5528f
Source dataset
uspto-grants-2005_05
Patent number
US06891066B2

Reaction notes

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