Formaldehyde → HCID 19607755, compound

HRID 1291619Notes

Reaction equation

HRID 1291619 reaction equation
N[CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([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)[CH2:3]1.C=O.[C:33]([BH3-])#[N:34].[Na+].[C:37](=O)([O-])[O-].[K+].[K+]>O.C(O)(=O)C.CO>[CH3:37][N:34]([CH3:33])[CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([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)[CH2:3]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 19607782HCID 19607782, compound

Product 1

HCID 19607755HCID 19607755, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 3-amino-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.5 g) are added methanol (10 ml), 37% formaline (0.8 ml) and sodium cyanoborohydride (0.16 g). To the mixture is added acetic acid (0.5 ml) under ice-cooling and the mixture is stirred at room temperature for 1 hour. Water is added to the reaction mixture and the mixture is basified with potassium carbonate and extracted with dichloromethane. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane→dichloromethane:methanol=20:1) to give 3-dimethylamino-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.3 g) as colorless amorphous.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. concentrationThe solvent is concentrated
  4. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane→dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-55d4f30ea7f84390843c9caed534810c
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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