Pyridine → HCID 56634222, compound

HRID 1247944Notes

Reaction equation

HRID 1247944 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([CH:6]=[C:7]2[C:16]3[N:15]=[C:14]4[CH:17]=[CH:18][C:19]([C:21]([OH:23])=[O:22])=[CH:20][N:13]4[C:12](=[O:24])[C:11]=3[CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].N1C=CC=CC=1>CN(C)C=O>[C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]2[C:16]3[N:15]=[C:14]4[CH:17]=[CH:18][C:19]([C:21]([OH:23])=[O:22])=[CH:20][N:13]4[C:12](=[O:24])[C:11]=3[CH2:10][CH2:9][CH2:8]2)=[CH:25][CH:26]=1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 56638271HCID 56638271, compound

Product 1

HCID 56634222HCID 56634222, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-amino-benzylidene)-1,2,3,4-tetrahydro-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid (1 g) in dimethylformamide (40 ml) was reacted with acetic anhydride (4 ml) in the presence of pyridine (8 ml) at 60° C. for 7 hours. After cooling and dilution with ice water, the precipitate was filtered and washed with water: crystallization from dimethylformamide-ethanol gave 0.7 g of 4-(4-acetylamino-benzylidene)-1,2,3,4-tetrahydro-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid.

Workup

  1. temperatureAfter cooling
  2. filtrationdilution with ice water, the precipitate was filtered
  3. washwashed with water
  4. customcrystallization from dimethylformamide-ethanol

Sources & evidence

ORD record
ord-7f68211b0f1e4f4795a39cf9626b22fa
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

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