Water → 5-((2-Chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid

HRID 928970Notes

Reaction equation

HRID 928970 reaction equation
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:3]=1[F:20].[CH3:21]C1C=CC(S(O)(=O)=O)=CC=1.O>C(OC)(OC)OC>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][C:4]1[C:5]([C:6]([OH:8])=[O:7])=[CH:9][C:10]2[O:11][CH:21]=[N:1][C:2]=2[C:3]=1[F:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 897049294-Amino-2-((2-chlorophenyl)amino)-3-fluoro-5-hydroxybenzoic acid

Product 1

HCID 897047945-((2-Chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

To a solution of 4-amino-2-((2-chlorophenyl)amino)-3-fluoro-5-hydroxybenzoic acid in trimethyl orthoformate (100 mL) was added p-TsOH (0.42 g, 1.35 mmol). The reaction mixture was stirred for 1 h and treated with water (300 mL). The precipitate was filtered off and the filter cake was washed with water to afford a yellow solid (12.31 g, 87.9% yield for two steps). 1H NMR (400 MHz, DMSO-d6): δ 13.9 (s, 1H), 9.05 (s, 1H), 8.8 (s, 1H), 8.23 (s, 1H), 7.43 (m, 1H), 7.15 (m, 1H), 6.98 (m, 1H), 6.74 (m, 1H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washthe filter cake was washed with water
  3. customto afford a yellow solid (12.31 g, 87.9% yield for two steps)

Sources & evidence

ORD record
ord-8b8107d94c874389aacff0c97170329d
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

Loading…