Sodium Hydroxide → HCID 19760243, compound

HRID 1586916Notes

Reaction equation

HRID 1586916 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([NH:17][C:18]3[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=3)=[O:16])=[CH:14][C:9]=2[C:8]([CH3:30])([CH3:29])[CH2:7][CH2:6][C:5]1=[O:31]>C(O)C.O1CCCC1>[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:27][CH:28]=3)=[O:16])=[CH:14][C:9]=2[C:8]([CH3:29])([CH3:30])[CH2:7][CH2:6][C:5]1=[O:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19760212HCID 19760212, compound

Product 1

HCID 19760243HCID 19760243, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1.69 ml of 3N sodium hydroxide solution were added to 1.00 g of ethyl p-(2,3,4,5-tetrahydro-1,5,5-trimethyl-2-oxo-1H-1-benzazepin-7-carboxamido)benzoate in 10 ml of ethanol/tetrahydrofuran (1:1). The reaction mixture was stirred at room temperature for 3 days and thereafter poured on to ice/conc. hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried and evaporated. Recrystallization from ethyl acetate yielded 0.81 g of p-(2,3,4,5-tetrahydro-1,5,5-trimethyl-2-oxo-1H-1-benzazepine-7-carboxamido)benzoic acid, m.p. >275° C.

Workup

  1. additionpoured on to ice/conc
  2. extractionhydrochloric acid and extracted with ethyl acetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. customdried
  5. customevaporated
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-49540305e1444c2e8c03a6aad40b80ac
Source dataset
uspto-grants-1993_06
Patent number
US05216148

Reaction notes

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