HCID 10638906, compound → HCID 19699066, compound

HRID 863028Notes

Reaction equation

HRID 863028 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)=[CH:6][CH:5]=1)([O-:3])=[O:2]>CO.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][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)=[CH:22][CH:23]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 10638906HCID 10638906, compound

Product 1

HCID 19699066HCID 19699066, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a mixture of 0.5 g of 5-(4-nitrobenzoyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine, O-acetate in 10 ml of methanol-water (8:2) is added KHCO3 and the mixture stirred at room temperature overnight. The mixture is concentrated under vacuum, diluted with 10 ml of water and extracted with ethyl acetate. The extract is dried (Na2SO4) and the solvent removed to give the product as a solid. Chromatography on silica gel with ethyl acetate as solvent gives crystals, m.p. 182°-185° C.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. additiondiluted with 10 ml of water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract is dried (Na2SO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-17d1e3952d84402fb9ecbf81737a72b5
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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