Water → HCID 10519066, compound

HRID 1733976Notes

Reaction equation

HRID 1733976 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][CH:13]([OH:17])[C:12]3[N:18]=[CH:19][CH:20]=[CH:21][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].O.C([O-])(O)=O.[Na+]>CS(C)=O.C(OC(=O)C)(=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]3[N:18]=[CH:19][CH:20]=[CH:21][C:11]2=3)=[O:9])=[CH:22][CH:23]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10638906HCID 10638906, compound

Product 1

HCID 10519066HCID 10519066, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.5 g of 5-(4-nitrobenzoyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine in 5 ml of dimethyl sulfoxide and 1 ml of acetic anhydride is stirred at room temperature 16 hours. To the mixture is added 10 ml of water and 1N NaHCO3. The mixture is extracted with ethyl acetate and the extract washed with water, 1N NaHCO3, brine and dried. The solvent is removed to give a solid. chromatography on silica gel with ethyl acetate as solvent gives the product as a solid, m.p. 188°-190° C.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washthe extract washed with water, 1N NaHCO3, brine
  3. customdried
  4. customThe solvent is removed
  5. customto give a solid

Sources & evidence

ORD record
ord-6f5f31d1319347efb889b6c4a6aced8c
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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