Sodium Hydroxide → 2-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid

HRID 1469721Notes

Reaction equation

HRID 1469721 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67971274Methyl 2-chloro-5-(pivalamidomethyl)benzoate

Product 1

HCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidYield 94.7%

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-5-(pivalamidomethyl)benzoate (2.00 g, 7.05 mmol) in THF:MeOH:H2O (3:2:1; 6 mL) and NaOH (564 mg, 14.1 mmol) to afford 1.8 g of the title product. 1H NMR (300 MHz, DMSO d6): 12.3 (br s, 1H), 8.14 (br t, 1H), 7.61 (s, 1H), 7.47-7.44 (d, J=8.1 Hz, 1H), 7.34-7.32 (d, J=7.8 Hz, 1H), 4.22 (d, J=6.0 Hz, 2H), 1.18 (s, 9H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-504e44b4ea9341bca0b32c9ea2c45547
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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