Ethanol → N-(6,7-dimethoxyquinolin-4-yl)-N-methyl-benzene-1,4-diamine

HRID 573434Notes

Reaction equation

HRID 573434 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[N:15]([CH3:25])[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C.CN(C)C=O.C(Cl)Cl>[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[N:15]([CH3:25])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 89581532(6,7-Dimethoxyquinolin-4-yl)methyl(4-nitrophenyl)amine

Product 1

HCID 89580706N-(6,7-dimethoxyquinolin-4-yl)-N-methyl-benzene-1,4-diamineYield 66.1%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

(6,7-Dimethoxyquinolin-4-yl)-methyl-(4-nitrophenyl)amine (0.30 g, 0.88 mmol), potassium carbonate (1.3 g, 9.4 mmol) and palladium hydroxide (1.00 g, 7.12 mmol) was hydrogenated in a mixture of ethanol (32 mL, 540 mmol), N,N-dimethylformamide (5 mL, 60 mmol) and methylene chloride (19 mL, 290 mmol) at 40 psi overnight. The mixture was filtered through Celite, and washed with calcium carbonate solution and brine then dried over sodium sulfate and concentrated to yield a crude product. This material was purified by prep. HPLC to yield [N-(6,7-Dimethoxy-quinolin-4-yl)-N-methyl-benzene-1,4-diamine (0.180 g, 66%). LCMS m/z=310 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with calcium carbonate solution and brine
  3. dry with materialthen dried over sodium sulfate
  4. concentrationconcentrated
  5. customto yield a crude product
  6. customThis material was purified by prep

Sources & evidence

ORD record
ord-47f4e9309d294f22919b91f3f658aa96
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

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