Sodium Hydroxide → 4-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)isophthalamic acid

HRID 988732Notes

Reaction equation

HRID 988732 reaction equation
[C:1]([C:5]1[CH:33]=[CH:32][C:8]([C:9]([NH:11][C:12]2[CH:27]=[CH:26][C:25]([C:28]([O:30]C)=[O:29])=[CH:24][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)=[O:15])=[O:10])=[CH:32][CH:33]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 219063172-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)-5-methoxycarbonylbenzamide

Product 1

HCID 219065324-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)isophthalamic acidYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into 5 mL MeOH was dissolved 91 mg (0.195 mmol) 2-(4-tert-butylbenzoylamino)-N-(5-chloropyridin-2-yl)-5-methoxycarbonylbenzamide, followed by 0.47 mL of 0.5 N (0.23 mmol) NaOH. The mixture was stirred 16 h, evaporated, diluted with 39.0 mL water, and extracted with 15 mL EtOAc-15 mL hexane mixture. The aquous layer was acidified with dilute HCl and extracted with 30 mL EtOH. The organic layer was dried (MgSO4) and evaporated, giving 43 mg (.49%) title compound.

Workup

  1. customevaporated
  2. additiondiluted with 39.0 mL water
  3. extractionextracted with 15 mL EtOAc-15 mL hexane mixture
  4. extractionextracted with 30 mL EtOH
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-7849a28d5d7a4e978c23d3a2c7c42881
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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