Dimethylformamide → HCID 21715715, compound

HRID 1603100Notes

Reaction equation

HRID 1603100 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12](=[O:30])[C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)=[CH:15][CH:14]=2)[CH2:4][CH2:3]1.CN.[CH3:33][N:34](C)C=O>CO>[CH3:33][NH:34][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12](=[O:30])[C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=3)=[CH:17][CH:18]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6329MethylamineHCID 18919728HCID 18919728, compound

Product 1

HCID 21715715HCID 21715715, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-oxo-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline(0.5 g) are added 40% solution of methylamine in methanol (5 ml), molecular sieves 4A (1 g) and dimethylformamide (6 ml), and the mixture is refluxed for 4 hours. After cooling, the reaction mixture is filtered and to the filtrate is added sodium borohydride (80 mg), and the mixture is stirred at room temperature for 1 hour. The reaction mixture is concentrated and water is added to the resulting residue, and extracted with ethyl acetate. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1) to give 4-methylamino-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.2 g) as colorless amorphous.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered and to the filtrate
  4. additionis added sodium borohydride (80 mg)
  5. concentrationThe reaction mixture is concentrated
  6. additionwater is added to the resulting residue
  7. extractionextracted with ethyl acetate
  8. concentrationThe solvent is concentrated
  9. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-607fd7f286c843a781f156d792e6cd63
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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