Hydrochloric Acid → HCID 54710192, compound

HRID 1080651Notes

Reaction equation

HRID 1080651 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 10 chromatography on silica gel eluting with chloroform-methanol (30:1) to give crystals of 2,3-dihydro-9-acetylamino-7-hydroxy-6-(1-indolinyl-carbonyl)-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 10 chromatography on silica gel eluting with chloroform-methanol (30:1)

Sources & evidence

ORD record
ord-ba68fe287bce4f4c8f56d8f9d6806d54
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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