Aluminium lithium hydride → 2,5-dimethyl-N-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-amine

HRID 735202Notes

Reaction equation

HRID 735202 reaction equation
C(O[C:4]([N:6]1[CH2:27][CH2:26][C:9]2[N:10]([CH3:25])[C:11]3[C:12]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=4)=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][N:6]1[CH2:27][CH2:26][C:9]2[N:10]([CH3:25])[C:11]3[C:16]([C:8]=2[CH2:7]1)=[CH:15][CH:14]=[CH:13][C:12]=3[NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68816344Ethyl-5-methyl-6-(4-toluidino)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 688158882,5-dimethyl-N-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-amineYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-5-methyl-6-(4-toluidino)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (73 mg, 0.214 mmol) was dissolved in anhydrous THF (1 mL) under N2 and LAH (1M in THF, 0.42 mmol) was added slowly. The reaction was brought to reflux for 2 hours. The reaction was quenched by the addition of water (16 μL), 15% aq. NaOH (16 μL) and then water (49 μL). The reaction was allowed to stir for 10 minutes between each addition. The aluminum salts were removed by filtration. The filtrate was evaporated and purified by silica gel column chromatography (10%, then 20% EtOAc-Hex) to give 2,5-dimethyl-N-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-amine (15 mg, 23%). 1H NMR (CDCl3, 300 MH2) δ 7.23-7.27 (m, 1H), 6.89-7.03 (m, 3H), 6.88 (d, 1H, J=7.3 Hz), 6.54 (d, 2H, J=8.4 Hz), 3.70 (s, 5H), 2.79-2.89 (m, 4H), 2.58 (s, 3H), 2.23 (s, 3H) ppm.

Workup

  1. temperatureto reflux for 2 hours
  2. customThe reaction was quenched by the addition of water (16 μL), 15% aq. NaOH (16 μL)
  3. customThe aluminum salts were removed by filtration
  4. customThe filtrate was evaporated
  5. custompurified by silica gel column chromatography (10%

Sources & evidence

ORD record
ord-13c573b6c00e40c7ba6824eb1ea350b4
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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