Acetic Acid → HCID 13345730, compound

HRID 325852Notes

Reaction equation

HRID 325852 reaction equation
[CH3:1][CH:2]1[N:7]2[CH:8]=[C:9]([C:22]([O:24]CC)=[O:23])[C:10](=[O:21])[C:11]3[CH:12]=[CH:13][C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:5]([C:6]=32)[O:4][CH2:3]1.C(O)(=O)C.Cl>O>[CH3:1][CH:2]1[N:7]2[CH:8]=[C:9]([C:22]([OH:24])=[O:23])[C:10](=[O:21])[C:11]3[CH:12]=[CH:13][C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:5]([C:6]=32)[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 13345729HCID 13345729, compound

Product 1

HCID 13345730HCID 13345730, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11.5 g of ethyl 2,3-dihydro-3-methyl-7-oxo-10-phenyl-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate and 75 ml of glacial acetic acid was heated to reflux temperature and 75 ml of 6 N hydrochloric acid was subsequently added. Refluxing was continued for one hour after which time 150 ml of water was added. The solution was cooled and filtered to provide light brown solid 2,3-dihydro-3-methyl-7-oxo-10-phenyl-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, m.p. 295°-296° C. Recrystallization from aqueous N,N-dimethylformamide gave light yellow crystals. Analysis: Calculated for C19H15NO4 : %C, 71.0; %H, 4.7; %N, 4.4; Found: %C, 70.4; %H, 4.6; %N, 4.3. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperaturewas heated
  2. additionwas subsequently added
  3. temperatureRefluxing
  4. temperatureThe solution was cooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4031e9a82bf549dabee976dd3257fea3
Source dataset
uspto-grants-1984_04
Patent number
US04443447

Reaction notes

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