Sodium Acetate → HCID 14501361, compound

HRID 1904597Notes

Reaction equation

HRID 1904597 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([F:29])=[C:10]([F:28])[C:11]3[C:21](=[O:22])[C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][N:13]4[C@@H:14]([CH3:18])[CH2:15][O:16][C:17]=2[C:12]=34)[CH:5]=[C:4]([CH3:30])[N:3]=1.C([O-])(=O)C.[Na+]>Cl>[CH3:30][C:4]1[CH:5]=[C:6]([C:8]2[C:9]([F:29])=[C:10]([F:28])[C:11]3[C:21](=[O:22])[C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:13]4[C@@H:14]([CH3:18])[CH2:15][O:16][C:17]=2[C:12]=34)[CH:7]=[C:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 14501359ethyl (S)-10-(2,6-dimethyl-4-pyridinyl)-8,9-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate

Product 1

HCID 14501361HCID 14501361, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.20 g ethyl (S)-10-(2,6-dimethyl-4-pyridinyl)-8,9-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate in 15 ml 1M hydrochloric acid was heated at reflux for 2 hours. The reaction mixture was cooled, poured into sodium acetate solution and extracted with methylene dichloride. The extract was dried (sodium sulfate) and concentrated, and the residue was crystallized from methanol to give 0.58 g (S)-10-(2,6-dimethyl-4-pyridinyl)-8,9-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid as a colorless solid, m.p. 307°-310° C., [α]D25 =-39.1° (1% in chloroform).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with methylene dichloride
  4. dry with materialThe extract was dried (sodium sulfate)
  5. concentrationconcentrated
  6. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-4f544419b7b4475cabbee7bf6f5bbe0a
Source dataset
uspto-grants-1989_06
Patent number
US04839355

Reaction notes

Loading…