Hydroxyamine hydrochloride → 7-(1-Hydroxyimino-ethyl)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester

HRID 33209Notes

Reaction equation

HRID 33209 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][C:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12][C:6]=2[CH:5]=1)(=O)[CH3:2].Cl.[NH2:23][OH:24]>N1C=CC=CC=1>[C:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([C:1](=[N:23][OH:24])[CH3:2])[CH:21]=[CH:20][C:7]=2[CH2:8][CH2:9]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 18173273tert-butyl 7-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate

Product 1

HCID 865941687-(1-Hydroxyimino-ethyl)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl esterYield 66.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Acetyl-3-(tert-butyloxycarbonyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (8.9 g, 30.8 mmol) was dissolved in pyridine (30 ml) and hydroxylamine hydrochloride (2.3 g, 33 mmol) was added and the mixture stirred for 2 h at room temperature. The solvent was evaporated and hexane (300 ml) and water (100 ml) were added and the colourless precipitate was filtered and washed with hexane (3×100 ml). The compound was dried in vacuo to give the title compound (6.23 g, 66%).

Workup

  1. customThe solvent was evaporated
  2. additionhexane (300 ml) and water (100 ml) were added
  3. filtrationthe colourless precipitate was filtered
  4. washwashed with hexane (3×100 ml)
  5. customThe compound was dried in vacuo

Sources & evidence

ORD record
ord-ce4ab795e23b4b43a6a95d6fb5beeca9
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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