Hydrochloric Acid → HCID 54710192, compound

HRID 1598553Notes

Reaction equation

HRID 1598553 reaction equation
C([O:4][C:5]1[C:14]2[CH:15]=[C:16]([NH2:18])[CH:17]=[C:12]3[C:13]=2[N:8]([CH2:9][CH2:10][O:11]3)[C:7](=[O:19])[C:6]=1[C:20]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1)=[O:21])(=O)C.[C:31](=[O:34])([O-])[O-].[K+].[K+].Cl.[CH3:38]N(C)C=O>>[C:31]([NH:18][C:16]1[CH:17]=[C:12]2[O:11][CH2:10][CH2:9][N:8]3[C:7](=[O:19])[C:6]([C:20]([N:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH2:24][CH2:23]4)=[O:21])=[C:5]([OH:4])[C:14]([CH:15]=1)=[C:13]23)(=[O:34])[CH3:38]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18929650HCID 18929650, compound

Product 1

HCID 54710192HCID 54710192, compound

Procedure

A mixture of 2,3-dihydro-7-acetoxy-9-amino-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (1.5 g) and potassium carbonate (0.5 g) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 1 hour. The mixture was poured into cold diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and evaporated. The residue (1 g) was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1) to give crystals of 2,3-dihydro-9-acetylamino-7-hydroxy-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (0.72 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customevaporated
  4. customThe residue (1 g) was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1)

Sources & evidence

ORD record
ord-fce17d41fed14a6d9d42f4651e6d684d
Source dataset
uspto-grants-1998_04
Patent number
US05739130

Reaction notes

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