Sodium Hydroxide → 6-Chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acid

HRID 1469788Notes

Reaction equation

HRID 1469788 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:18])[CH3:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86692264Ethyl 6-chloro-2-fluoro-3-(isobutyramidomethyl)benzoate

Product 1

HCID 866922656-Chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acidYield 88.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The title compound was prepared following the procedure described in Intermediate-2, step-3 using ethyl 6-chloro-2-fluoro-3-(isobutyramidomethyl)benzoate (1.00 g, 3.31 mmol) and NaOH (530 mg, 13.26 mmol) in THF:MeOH:H2O (3:2:1; 12 mL) to afford 800 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 14.10 (s, 1H), 8.32 (br t, 1H), 7.38-7.29 (m, 2H), 4.25 (d, J=5.1 Hz, 2H), 2.40 (m, 1H), 1.00 (d, J=6.9 Hz, 6H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d556770182df42ca947ca94d9d866d84
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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