HCID 19608045, compound → HCID 19607782, compound

HRID 1603097Notes

Reaction equation

HRID 1603097 reaction equation
C(OC([NH:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:22](=[O:40])[C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:39])[C:31]3[CH:36]=[C:35]([Cl:37])[CH:34]=[C:33]([Cl:38])[CH:32]=3)=[CH:25][CH:24]=2)[CH2:13]1)=O)C1C=CC=CC=1.[H][H]>[Pd].C(O)(=O)C>[NH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:22](=[O:40])[C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:39])[C:31]3[CH:36]=[C:35]([Cl:37])[CH:34]=[C:33]([Cl:38])[CH:32]=3)=[CH:27][CH:28]=2)[CH2:13]1

Participants

5

Reactant 2

HCID 19608045HCID 19608045, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19607782HCID 19607782, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To 3-benzyloxycarbonylamino-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (3.3 g) are added acetic acid (40 ml) and 10% Pd-C (0.4 g) and the reaction mixture is subjected to catalytic reduction at ordinary temperature under atmospheric pressure of hydrogen. One hour thereafter, the catalyst is removed by filtration and the filtrate is concentrated. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1), and recrystallized from ethanol to give 3-amino-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (1.6 g) as white powder, m.p. 207-210° C.

Workup

  1. customOne hour thereafter, the catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1)
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7598c83aca7c40018504ebc3b03625f3
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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