Ethyl 5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate → ethyl 6-amino-5-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

HRID 735200Notes

Reaction equation

HRID 735200 reaction equation
[CH3:1][N:2]1[C:10]2[C:9]([N+:11]([O-])=O)=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[CH2:14][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17][C:3]1=2>CCO.[OH-].[Pd+2].[OH-]>[NH2:11][C:9]1[C:10]2[N:2]([CH3:1])[C:3]3[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C:4]=3[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 68815911Ethyl 5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 68816953ethyl 6-amino-5-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylateYield 66%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Ethyl 5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (340 mg, 1.12 mmol) and palladium hydroxide (60 mg) were dissolved in EtOH (50 mL) and stirred for 18 h under H2 (55 psi). The mixture was filtered through Celite and the filtrate was evaporated to give ethyl 6-amino-5-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate as a light tan solid (202 mg, 66%). 1H NMR (CDCl3, 300 MH) δ 6.85-7.02 (m, 2H), 6.43-6.51 (d, 1H, J=7.0 Hz), 4.80 (br. s, 2H), 4.21 (q, 2H, J=6.6 Hz), 3.90 (s, 3H), 3.80-3.88 (m, 2H), 2.75-2.80 (m, 2H), 1.27 (t, 3H, J=7.3 Hz) ppm.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-88c9bb82ba844f548e96a1599591d835
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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