Hydroxyamine hydrochloride → HCID 23333613, compound

HRID 904195Notes

Reaction equation

HRID 904195 reaction equation
[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[C:4]2[CH:14]=[C:15]([CH2:18][C:19]([O:21]C)=O)[CH:16]=[CH:17][C:3]1=2.Cl.[NH2:24][OH:25].C[O-].[Na+]>CO>[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[C:4]2[CH:14]=[C:15]([CH2:18][C:19]([NH:24][OH:25])=[O:21])[CH:16]=[CH:17][C:3]1=2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 23333585HCID 23333585, compound

Product 1

HCID 23333613HCID 23333613, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 5,6-dihydro-5-methyl-11-oxodibenz[b,e]azepine-2-acetate (1.5 g) was dissolved in methanol (80 ml), and hydroxylamine hydrochloride (1.0 g) was added to make a homogeneous solution. Then, a 28% solution (6 g) of sodium methylate in methanol was added to the homogeneous solution, and the mixture was heated for 3 hours. Then, the reaction mixture was concentrated, and after addition of water (20 ml) and dry ice (1 g), was extracted with chloroform. The extract was dried over MgSO4, and then, chloroform was distilled off. The residue was stirred with benzene to form crystals. The crystals were recrystallized from benzene-tetrahydrofuran to obtain the desired compound (0.8 g) as yellow prismatic crystals.

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. concentrationThen, the reaction mixture was concentrated
  3. additionafter addition of water (20 ml) and dry ice (1 g)
  4. extractionwas extracted with chloroform
  5. dry with materialThe extract was dried over MgSO4
  6. distillationchloroform was distilled off
  7. customto form crystals
  8. customThe crystals were recrystallized from benzene-tetrahydrofuran

Sources & evidence

ORD record
ord-471b583442ef45a69a3b67a2f3fb1222
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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