Methyl 1-methyl-8-nitro-1,2-dihydroquinoline-7-carboxylate → Methyl 8-amino-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 925620Notes

Reaction equation

HRID 925620 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:15]([O:17][CH3:18])=[O:16])[C:10]=2[N+:12]([O-])=O)[CH:5]=[CH:4][CH2:3]1>CO.[Pd]>[NH2:12][C:10]1[C:9]([C:15]([O:17][CH3:18])=[O:16])=[CH:8][CH:7]=[C:6]2[C:11]=1[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]2

Participants

4

Reactant 1

HCID 71014122Methyl 1-methyl-8-nitro-1,2-dihydroquinoline-7-carboxylate

Product 1

HCID 89188582Methyl 8-amino-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 1-methyl-8-nitro-1,2-dihydroquinoline-7-carboxylate (1.25 g, 5.04 mmol) in degassed MeOH (25 mL) at rt was added Pd/C (125 mg). The mixture was stirred under 1 atm H2 for 16 h. The resulting mixture was filtered through celite and concentrated to afford methyl 8-amino-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylate in pure form.

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9630e0427992450aa3e642abcbe85c7c
Source dataset
uspto-grants-2016_03
Patent number
US09284312B2

Reaction notes

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