Water → 2,3,4,5-tetrahydro-1H-1-benzazepine-2,5-dione

HRID 2119985Notes

Reaction equation

HRID 2119985 reaction equation
[H-].[Na+].C([O:5][C:6](=O)[CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])=[O:10])C.O>C1COCC1>[NH:17]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:9](=[O:10])[CH2:8][CH2:7][C:6]1=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 21283602Ethyl 4-(2-aminophenyl)-4-oxobutanoate

Product 1

HCID 3693982,3,4,5-tetrahydro-1H-1-benzazepine-2,5-dioneYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (10 mg, 0.43 mmol) in dry THF (1 mL) was added 4-(2-amino-phenyl)-4-oxo-butyric acid ethyl ester (80 mg, 0.36 mmol) under Argon at −40° C. The reaction mixture was then allowed to warm up to rt over 3 h, and then added to water (20 mL). The mixture was then extracted with DCM (3×15 mL) and the combined extracts were then dried (sodium sulfate), and evaporated to leave an off-white solid. Recrystallization from EtOAc afforded a white solid (51 mg, 81%), m/z 175 (M).

Workup

  1. extractionThe mixture was then extracted with DCM (3×15 mL)
  2. dry with materialthe combined extracts were then dried (sodium sulfate)
  3. customevaporated
  4. customto leave an off-white solid
  5. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-5ea0ac506de94e1ca90453849bbf16c6
Source dataset
uspto-grants-2004_02
Patent number
US06686352B2

Reaction notes

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