Acetic Anhydride → HCID 86739361, compound

HRID 325859Notes

Reaction equation

HRID 325859 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:26]3=[C:27]4[N:22]([CH:23]([CH3:28])[CH2:24][CH2:25]3)[CH:21]=[C:20]([C:29]([OH:31])=[O:30])[C:19](=[O:32])[C:18]4=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>C(O)=O>[OH2:3].[CH:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:26]3=[C:27]4[N:22]([CH:23]([CH3:28])[CH2:24][CH2:25]3)[CH:21]=[C:20]([C:29]([OH:31])=[O:30])[C:19](=[O:32])[C:18]4=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13345740HCID 13345740, compound

Product 1

HCID 86739361HCID 86739361, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a hot mixture of 20 ml of 97% formic acid and 10 ml of acetic anhydride was added 1.5 g of 8-(4-aminophenyl)-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo-[ij]quinolizine-2-carboxylic acid. The mixture was heated on a steam bath for 15 minutes and then evaporated. The residue was triturated with water to provide a solid. The solid was recrystallized from glacial acetic acid to provide 6,7-dihydro-8-(4-formamidophenyl)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid hydrate, m.p. >300° C. Analysis: Calculated for C21H18N2O4.1/3H2O: %C, 68.5; %H, 5.1; %N, 7.6; Found: %C, 68.8; %H, 5.2; %N, 7.6. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperatureThe mixture was heated on a steam bath for 15 minutes
  2. customevaporated
  3. customThe residue was triturated with water
  4. customto provide a solid
  5. customThe solid was recrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-0a4db18f79de421e8ce7c2d2adc0628d
Source dataset
uspto-grants-1984_04
Patent number
US04443447

Reaction notes

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