Sodium Hydroxide → 2-Chloro-4-fluoro-5-(pivalamidomethyl)benzoic acid

HRID 1469790Notes

Reaction equation

HRID 1469790 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([CH2:13][NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([CH2:13][NH:14][C:15](=[O:20])[C:16]([CH3:18])([CH3:17])[CH3:19])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86692266Methyl 2-chloro-4-fluoro-5-(pivalamidomethyl)benzoate

Product 1

HCID 866922682-Chloro-4-fluoro-5-(pivalamidomethyl)benzoic acidYield 83.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The title compound was prepared following the procedure described in step-3 of Intermediate-2 using methyl 2-chloro-4-fluoro-5-(pivalamidomethyl)benzoate (250 mg, 0.83 mmol) in THF:MeOH:H2O (3:2:1; 6 mL) and NaOH (66 mg, 1.66 mmol) to afford 200 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.17-8.14 (t, J=6.0 Hz, 1H), 7.76-7.73 (d, J=8.4 Hz, 1H), 7.53-7.50 (d, J=9.9 Hz, 1H), 4.26 (d, J=5.7 Hz, 2H), 1.12 (s, 9H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-728d3239c513488aaea2a8f8797e0a7d
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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