Hydroxyamine hydrochloride → HCID 136130050, compound

HRID 2068561Notes

Reaction equation

HRID 2068561 reaction equation
[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][C:10](=O)[C:4]2=[N:3][CH:2]=1.Cl.[NH2:17][OH:18].CC([O-])=O.[Na+]>CO>[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][C:10](=[N:17][OH:18])[C:4]2=[N:3][CH:2]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 532420135,6-Dihydroimidazo[1,2-a][1]benzazepin-4-one2×

Product 1

HCID 136130050HCID 136130050, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, charge a reactor with 42 kg of (5,6-dihydroimidazo[1,2-a][1]benzazepin-4-one), 15.5 kg of hydroxylamine hydrochloride, 21.5 kg of sodium acetate anhydrous, and 171 kg of methanol. Heat the resulting brown suspension to 60 to 70° C. for 20 h (in process HPLC<3% 5,6-dihydroimidazo[1,2-a][1]benzazepin-4-one). Cool the reaction to 23 to 25° C. and stir for 8 h. Isolate the solid by centrifugation, rinsing with 33 kg of cold methanol. Transfer the resulting solid into a reactor and slurry with 210 kg of water at 85 to 90° C. for 2 h. Isolate the solid by centrifugation, rinsing the solid with 85 kg of water. Dry the resulting solid to give 39.65 kg of 5,6-dihydro-4H-benzo[f]imidazo[1,2-a]azepin-4-one oxime. MS=214 (M+1).

Workup

  1. temperatureCool
  2. customthe reaction to 23 to 25° C.
  3. customIsolate the solid by centrifugation
  4. washrinsing with 33 kg of cold methanol
  5. waitslurry with 210 kg of water at 85 to 90° C. for 2 h
  6. customIsolate the solid by centrifugation
  7. washrinsing the solid with 85 kg of water
  8. customDry the resulting solid

Sources & evidence

ORD record
ord-b9d6fd4e3e7e4b7fafd5e9c47cb14bc2
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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