HCID 10850137, compound → HCID 15308575, compound

HRID 234912Notes

Reaction equation

HRID 234912 reaction equation
[CH2:1]([C@@H:3]1[C:8](=[O:9])[N:7]([CH:10]([CH3:12])[CH3:11])[C:6]2[CH:13]=[CH:14][C:15]([C:17]([O:19]C)=[O:18])=[CH:16][C:5]=2[O:4]1)[CH3:2]>Cl>[CH2:1]([C@@H:3]1[C:8](=[O:9])[N:7]([CH:10]([CH3:12])[CH3:11])[C:6]2[CH:13]=[CH:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:5]=2[O:4]1)[CH3:2]

Participants

3

Reactant 1

HCID 10850137HCID 10850137, compound

Product 1

HCID 15308575HCID 15308575, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of (R)-2-ethyl-7-methoxycarbonyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (1.70 g) in concentrated hydrochloric acid (30 ml) was stirred under reflux for a day. The concentrated hydrochloric acid was distilled off under reduced pressure. Water was added to the residue and extraction with ethyl acetate was conducted. The extract was washed with water and then the solvent was distilled off under reduced pressure to give (R)-2-ethyl-4-(2-propyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid (1.60 g).

Workup

  1. temperatureunder reflux for a day
  2. distillationThe concentrated hydrochloric acid was distilled off under reduced pressure
  3. additionWater was added to the residue and extraction with ethyl acetate
  4. washThe extract was washed with water
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-705d364dbf8d46b3b1b156e74a787b4a
Source dataset
uspto-grants-1997_01
Patent number
US05597820

Reaction notes

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