1-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline → 1-Methyl-1,2,3,4-tetrahydroquinolin-7-amine

HRID 494172Notes

Reaction equation

HRID 494172 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[CH2:5][CH2:4][CH2:3]1>[Pd].CO>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4][CH2:3][N:2]2[CH3:1])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 114809551-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 112174211-Methyl-1,2,3,4-tetrahydroquinolin-7-amineYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-7-nitro-1,2,3,4-tetrahydroquinoline (D2) (5.35 g, 27.9 mmol) and 10% palladium on charcoal (2 g, 54% water) in methanol (150 ml) was hydrogenated at atmospheric pressure and ambient temperature temperature for 3 d. The catalyst was filtered off and washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the crude product, which was purified by flash column chromatography. Elution with 5-10% EtOAc/DCM gave the title compound as a brown oil (2.58 g). 1H NMR (250 MHz, CDCl3) δ(ppm): 6.73 (dd, 1H), 5.99 (m, 2H), 3.49 (br, 1H), 3.18 (m, 2H), 2.84 (s, 3H), 2.66 (t, 2H), 1.93 (m, 2H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with further methanol
  3. filtrationThe combined filtrated
  4. concentrationwashings were concentrated in vacuo
  5. customto give the crude product, which
  6. customwas purified by flash column chromatography
  7. washElution with 5-10% EtOAc/DCM

Sources & evidence

ORD record
ord-4e310a0df519445781979b6bdef880cb
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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