Hydroxyamine hydrochloride → HCID 178451593, compound

HRID 1514207Notes

Reaction equation

HRID 1514207 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11][C:5]=2[CH:4]=1)#[N:2].Cl.[NH2:22][OH:23].C(=O)(O)[O-].[Na+]>C(O)C>[OH:23][NH:22][C:1](=[NH:2])[C:3]1[CH:20]=[CH:19][C:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium BicarbonateHCID 18173275tert-Butyl 7-cyano-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate

Product 1

HCID 178451593HCID 178451593, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1,1-dimethylethyl 7-cyano-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (may be prepared as described in WO2002040471) (5 g, 18.36 mmol), hydroxylamine hydrochloride (2.55 g, 36.7 mmol) and sodium bicarbonate (7.71 g, 92 mmol) in ethanol (250 ml) was heated at 50° C. overnight. Further hydroxylamine hydrochloride (0.638 g, 9.18 mmol) was added to the reaction mixture and heating at 50° C. continued for 5 h. The reaction mixture was allowed to cool and the solid filtered off, the solution was concentrated in vacuo to yield the title compound as a white solid (5.77 g, 17.01 mmol, 93% yield). δH (d6DMSO, 400 MHz): 9.56 (1H, s), 7.52-7.37 (2H, m), 7.14 (1H, d), 5.77 (2H, br s), 3.50-3.32 (4H, m), 2.91-2.80 (4H, m), 1.41 (9H, s). MS (ES): C16H23N3O3 requires 305; found 306 [M+H]+.

Workup

  1. temperatureheating at 50° C.
  2. temperatureto cool
  3. filtrationthe solid filtered off
  4. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-fec3b730e37d487dbeacced12eb81940
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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