(S)-2,4-diethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine → (S)-2,4-diethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid

HRID 234915Notes

Reaction equation

HRID 234915 reaction equation
[CH2:1]([C@H:3]1[C:8](=[O:9])[N:7]([CH2:10][CH3:11])[C:6]2[CH:12]=[CH:13][C:14]([C:16]([O:18]C)=[O:17])=[CH:15][C:5]=2[O:4]1)[CH3:2]>Cl>[CH2:1]([C@H:3]1[C:8](=[O:9])[N:7]([CH2:10][CH3:11])[C:6]2[CH:12]=[CH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][C:5]=2[O:4]1)[CH3:2]

Participants

3

Reactant 1

HCID 10825426(S)-2,4-diethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 10776998(S)-2,4-diethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acidYield 81.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of (S)-2,4-diethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (1.90 g) in concentrated hydrochloric acid (40 ml) was stirred under reflux for a day. The concentrated hydrochloric acid was distilled off under reduced pressure to give (S)-2,4-diethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid (1.47 g).

Workup

  1. temperatureunder reflux for a day
  2. distillationThe concentrated hydrochloric acid was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dd073c96401043aeb09e1a4fdf2b4797
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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