Hydrochloric Acid → 6-(2-Chlorophenylamino)-7-fluoro-3-methylbenzo[c]-isoxazole-5-carboxylic acid

HRID 857514Notes

Reaction equation

HRID 857514 reaction equation
C[O:2][C:3]([C:5]1[C:14]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[C:13]([F:23])[C:8]2=[N:9][O:10][C:11]([CH3:12])=[C:7]2[CH:6]=1)=[O:4].C1COCC1.[Li+].[OH-].Cl>O>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C:14]1[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]2[C:8]([C:13]=1[F:23])=[N:9][O:10][C:11]=2[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 688605096-(2-Chlorophenylamino)-7-fluoro-3-methyl-benzo[c]-isoxazole-5-carboxylic acid methyl ester

Product 1

HCID 115805806-(2-Chlorophenylamino)-7-fluoro-3-methylbenzo[c]-isoxazole-5-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 6-(2-chlorophenylamino)-7-fluoro-3-methyl-benzo[c]-isoxazole-5-carboxylic acid methyl ester (55) (100 mg, 0.299 mmol) in 6:1 THF:water (3.5 mL) was added LiOH (0.60 ml of a 1 M solution in water). After 1 hour, the reaction was acidified to pH 1 with 1 N HCl, diluted with water and extracted with EtOAc. The combined organic extracts were washed with water, dried (MgSO4) and concentrated to give the desired product (56) (87 mg, 91%). MS APCI (−) m/z 319, 321 (M+, Cl pattern) detected: 1H NMR (400 MHz, CD3OD) δ 8.45 (s, 1H), 7.38 (dd, 1H), 7.20 (m, 1H), 6.91 (m, 2H), 2.88 (s, 3H): 19F NMR (376 MHz, CD3OD) −136.40 (s, 1F).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7bad4e21573c40c8bd5972853fb23806
Source dataset
uspto-grants-2006_12
Patent number
US07144907B2

Reaction notes

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