Acetic Anhydride → HCID 70468971, compound

HRID 746260Notes

Reaction equation

HRID 746260 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19]3=[C:20]4[N:15]([CH:16]([CH3:21])[CH2:17][CH2:18]3)[CH:14]=[C:13]([C:22]([OH:24])=[O:23])[C:12](=[O:25])[C:11]4=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(O)(=O)C>[OH2:23].[C:26]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19]3=[C:20]4[N:15]([CH:16]([CH3:21])[CH2:17][CH2:18]3)[CH:14]=[C:13]([C:22]([OH:24])=[O:23])[C:12](=[O:25])[C:11]4=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13345740HCID 13345740, compound

Product 1

HCID 70468971HCID 70468971, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.7 g (2.1 mmole) of 8-(4-aminophenyl)-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 5 ml of acetic acid and 2.5 ml of acetic anhydride was heated at its reflux temperature until solid was observed to precipitate. The mixture was diluted with 10 ml of water, stirred and cooled. The product was separated by filtration to provide 8-(4-acetamidophenyl)-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid hydrate, m.p. 168°-170° C. Analysis: Calculated for C22H20N2O4.0.75 H2O: %C, 67.8; %H, 5.6; %N, 7.2; Found: %C, 67.9; %H, 5.3; %N, 7.4. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperaturewas heated at its
  2. temperaturereflux temperature until solid
  3. customto precipitate
  4. additionThe mixture was diluted with 10 ml of water
  5. temperaturecooled
  6. customThe product was separated by filtration

Sources & evidence

ORD record
ord-a992d5c37f9248b0adbf456b51114dea
Source dataset
uspto-grants-1986_07
Patent number
US04603199

Reaction notes

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