HCID 619079, compound → HCID 612783, compound

HRID 2404235Notes

Reaction equation

HRID 2404235 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][C:7]([N+:15]([O-])=O)=[C:6]2[CH3:18].[H][H]>O1CCCC1.[Pd]>[NH2:15][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[CH3:18])=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=2

Participants

5

Reactant 2

HCID 619079HCID 619079, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 612783HCID 612783, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6,7-Dimethoxy-4-methyl-3-nitroquinoline (5.80 g, 23.36 mmol) is dissolved in tetrahydrofuran (60 ml). Palladium on carbon (5%, 2.90 g, water-moist) is subsequently added, and the suspension is stirred turbulently in a hydrogen atmosphere at room temperature for 16 h. When the reaction is complete, the solid material is filtered off with suction through kieselguhr and rinsed with tetrahydrofuran. The filtrate is evaporated to dryness in vacuo, giving 3-amino-6,7-dimethoxy-4-methylquinoline (4.05 g, 18.56 mmol) as a solid. MS: 219.0 (M+H+), TLC (HPTLC): Rf=0.35 (ethyl acetate/ethanol 8:1, parts by volume).

Workup

  1. filtrationthe solid material is filtered off with suction through kieselguhr
  2. washrinsed with tetrahydrofuran
  3. customThe filtrate is evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-0c83af514c12448d887e4897a68f6a94
Source dataset
uspto-grants-2014_08
Patent number
US08802712B2

Reaction notes

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