Acetic Anhydride → HCID 18929650, compound

HRID 1598552Notes

Reaction equation

HRID 1598552 reaction equation
[OH:1][C:2]1[C:11]2[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][O:8]3)[C:4](=[O:18])[C:3]=1[C:19]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1)=[O:20].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([O:1][C:2]1[C:11]2[CH:12]=[C:13]([NH2:15])[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][O:8]3)[C:4](=[O:18])[C:3]=1[C:19]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1)=[O:20])(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54710160HCID 54710160, compound

Product 1

HCID 18929650HCID 18929650, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2,3-dihydro-7-hydroxy-9-nitro-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (2.7 g) and acetic anhydride (0.79 g) in pyridine (4 ml) was stirred at room temperature for 1 hour. The mixture was concentrated in vacuo. The residue containing 2,3-dihydro-7-acetoxy-9-nitro-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine was reduced catalytically in a similar manner to that of Example 22 to give crystals of 2,3-dihydro-7-acetoxy-9-amino-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (1.7 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionThe residue containing 2,3-dihydro-7-acetoxy-9-nitro-6-(1-indolinylcarbonyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine

Sources & evidence

ORD record
ord-99e77ea7b0ec4528ba8c968a366efd58
Source dataset
uspto-grants-1998_04
Patent number
US05739130

Reaction notes

Loading…