Chloroacetyl chloride → HCID 70469656, compound

HRID 325858Notes

Reaction equation

HRID 325858 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.[Cl:26][CH2:27][C:28](Cl)=[O:29]>C(O)(=O)C>[OH2:23].[Cl:26][CH2:27][C:28]([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:29]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 13345740HCID 13345740, compound

Product 1

HCID 70469656HCID 70469656, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 0.8 g sample of 8-(4-aminophenyl)-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid in 5 ml of hot acetic acid was added dropwise 0.3 ml of chloroacetyl chloride. The resulting solution was cooled and stirred for 20 minutes and then filtered. The solid was dried to provide golden crystals of 8-(4-chloroacetamidophenyl)-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid hydrate, m.p. 297° C. Analysis: Calculated for C22H19N2O4Cl.0.5H2O: %C, 63.4; %H, 4.6; %N, 6.7; Found: %C, 62.9; %H, 4.8; %N, 6.7. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperatureThe resulting solution was cooled
  2. filtrationfiltered
  3. customThe solid was dried

Sources & evidence

ORD record
ord-1182955cd2fb4598a041a5fd22f2963e
Source dataset
uspto-grants-1984_04
Patent number
US04443447

Reaction notes

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