Hydroxyamine hydrochloride → HCID 86616068, compound

HRID 2353905Notes

Reaction equation

HRID 2353905 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C:10](=O)[C:9]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:8]1=2)=[O:6])([CH3:3])[CH3:2].Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+]>CCO.O>[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C:10](=[N:21][OH:22])[C:9]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:8]1=2)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 68679200HCID 68679200, compound

Product 1

HCID 86616068HCID 86616068, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 8-Chloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester (3.40 g, 12.1 mmole) in EtOH/H2O (96.0 ml/24.0 ml) was added hydroxylamine hydrochloride (8.39 g, 121 mmole) followed by sodium acetate (9.93 g, 121 mmole). The reaction was heated under 60° C. for 3 hours. The mixture was partitioned between ethyl acetate (100 ml) and 1.00N HCl (100 ml). After separated the two layers, the aqueous layer was extracted with more acetate (2×100 ml). The combined organics washed with NaHCO3 (aq) and followed by brine (2×200 ml). Dried over Na2SO4, filtered and concentrated to provide the crude product (3.45 g, 96%), which was used directly for the next step without further purification. MS (ES+): 297 (M+H).

Workup

  1. customThe mixture was partitioned between ethyl acetate (100 ml) and 1.00N HCl (100 ml)
  2. customAfter separated the two layers
  3. extractionthe aqueous layer was extracted with more acetate (2×100 ml)
  4. washThe combined organics washed with NaHCO3 (aq)
  5. dry with materialDried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-293c8989f3054eac9bd2da65eea1eab2
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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