Ammonia → HCID 18929624, compound

HRID 1080648Notes

Reaction equation

HRID 1080648 reaction equation
Cl[C:2]1[C:11]2[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][O:8]3)[C:4](=[O:17])[C:3]=1[C:18]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)=[O:19].[NH3:29]>C(O)C.C(Cl)(Cl)Cl>[NH2:29][C:2]1[C:11]2[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][O:8]3)[C:4](=[O:17])[C:3]=1[C:18]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)=[O:19]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18929616HCID 18929616, compound

Product 1

HCID 18929624HCID 18929624, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,3-dihydro-7-chloro-9-methoxy-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (1 g), ammonia in ethanol (13 ml) and chloroform (20 ml) was heated at 100° C. in a sealed tube for 4 days. The solvent was evaporated and the residue was purified by column chromatography on silica gel eluting with chloroform-methanol (20:1) to give crystals of 2,3-dihydro-7-amino-9-methoxy-6-(1-indolinyl-carbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (0.35

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (20:1)

Sources & evidence

ORD record
ord-ae7cce8772194fb0a4eda9bde2de7f95
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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