Hydrochloric Acid → HCID 54710207, compound

HRID 1080649Notes

Reaction equation

HRID 1080649 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[N+:14]([C:17]1[CH:18]=[C:19]2[O:24][CH2:23][CH2:22][N:21]3C([O:27][C:28]([C:30]([CH:31]=1)=[C:20]23)=O)=O)([O-:16])=[O:15].Cl>CN(C)C(=O)C>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[N:21]2[CH2:22][CH2:23][O:24][C:19]3[C:20]2=[C:30]([CH:31]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=3)[C:28]=1[OH:27])=[O:4])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 54298606HCID 54298606, compound

Product 1

HCID 54710207HCID 54710207, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of diethyl malonate (0.54 g) in N,N-dimethylacetamide (10 ml) was added sodium hydride (60%; 135 mg), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added 3,4-dihydro-7-nitro-2H-1,4-benzoxazine-4,5-dicarboxylic anhydride (0.73 g), and the mixture was stirred at 120° C. for 2 hours. The mixture was poured into diluted HCl, and the precipitates were collected and washed with water to afford yellow crystals of 2,3-dihydro-6-ethoxycarbonyl-7-hydroxy-9-nitro-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (0.85 g).

Workup

  1. stirringthe mixture was stirred at 120° C. for 2 hours
  2. customthe precipitates were collected
  3. washwashed with water

Sources & evidence

ORD record
ord-961ea4177ae8426b9121a0c2ce295cd1
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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