N,N-Dimethylaniline → HCID 44269450, compound

HRID 1263318Notes

Reaction equation

HRID 1263318 reaction equation
Br[C:2]1(Br)[C:7]2=[N:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[C:11](=[O:12])[N:6]2[CH:5]([CH3:16])[CH2:4][CH2:3]1.[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C)C1C=CC=CC=1>CS(C)=O>[C:18]1([NH:24][N:25]=[C:2]2[C:7]3=[N:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[C:11](=[O:12])[N:6]3[CH:5]([CH3:16])[CH2:4][CH2:3]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 7516PhenylhydrazineHCID 13312949HCID 13312949, compound

Product 1

HCID 44269450HCID 44269450, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.73 g. (0.002 moles) of 9,9-dibromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid are dissolved in 2 ml. of dimethyl sulfoxide. To the solution 0.2 ml. (0.002 moles) of phenyl hydrazine and 0.5 ml. (0.004 moles) of N,N-dimethylaniline are added. Thereafter the reaction mixture is allowed to stand for three days. The precipitated crystals are filtered off and washed with methanol. The product is purified by alkaline/acidic precipitation. 0.4 g. (64.0%) of 9-(phenylhydrazono)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid are obtained, melting at 254° to 255° C.

Workup

  1. filtrationThe precipitated crystals are filtered off
  2. washwashed with methanol
  3. customThe product is purified by alkaline/acidic precipitation

Sources & evidence

ORD record
ord-73fdbb194c2b4d8abcc9295e9625d91b
Source dataset
uspto-grants-1984_06
Patent number
US04456752

Reaction notes

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