Dimethylformamide → HCID 23467113, compound

HRID 443383Notes

Reaction equation

HRID 443383 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:5]2[C:10]([C:11]=1[CH:12]=O)=[CH:9][C:8]([O:14][CH3:15])=[C:7]([O:16][CH3:17])[CH:6]=2.[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28]CN.[CH3:32][N:33](C)C=O>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:5]2[C:10]([C:11]=1[CH2:12][CH2:28][CH2:27][N:26]([CH3:31])[CH3:25])=[C:9]([CH2:32][NH2:33])[C:8]([O:14][CH3:15])=[C:7]([O:16][CH3:17])[CH:6]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 23467114HCID 23467114, compound

Product 1

HCID 23467113HCID 23467113, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.62 g 3-Chloro-1-(4-chlorophenyl)-6,7-dimethoxy-isoquinoline-4-aldehyde is heated to 80° C. within 4 hours in conjunction with 3.06 g of 3-dimethylaminopropylamine in 100 ml dimethylformamide (DMF) and 50 ml CH3OH. The solvent is removed in vacuo, the residue is dissolved in 150 ml of anhydrous methanol and 1.53 g of sodium boron hydride are added portionwise at 10° C. The reaction mixture is stirred for 3 hours, the solvent is removed in vacuo and the residue is stirred with water. Filtration of the resulting mixture gives 4.2 g 3-chloro-1-(4-chlorophenyl)-6,7-dimethoxy-4-(3-dimethylaminopropyl)-aminomethyl-isoquinoline having a melting point from 126° to 127° C.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in 150 ml of anhydrous methanol
  3. addition1.53 g of sodium boron hydride are added portionwise at 10° C
  4. customthe solvent is removed in vacuo
  5. stirringthe residue is stirred with water
  6. filtrationFiltration of the resulting mixture

Sources & evidence

ORD record
ord-ec6d163ab7104203b6d4a63a6876f102
Source dataset
uspto-grants-1981_04
Patent number
US04260611

Reaction notes

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