Methyl 3-methoxy-4-((1-methyl-5-nitro-1H-indol-3-yl)methyl)benzoate → Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

HRID 1198190Notes

Reaction equation

HRID 1198190 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=2)[N:16]([CH3:26])[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]>O1CCCC1.[Pd]>[NH2:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:26])[CH:15]=[C:14]2[CH2:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 11772604Methyl 3-methoxy-4-((1-methyl-5-nitro-1H-indol-3-yl)methyl)benzoate

Product 1

HCID 11209537Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoateYield 109.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)benzoate (1.5 grams) in 50 mL of tetrahydrofuran was hydrogenated at 40 p.s.i. in the presence of 10% palladium-on-carbon (0.3 grams) for 3 hours. The reaction was filtered and the filtrate evaporated to give 1.5 grams of title compound. NMR (CDCl3) δ:3.35, (broad s, 2H), 3.65 (s, 3H), 3.95 (s, 3H), 4.05 (s, 2H), 6.85 (m, 3H), 7.10 (m, 2H), 7.50 (m, 2H).

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a52e81431c4e42089f887b25d8af2e49
Source dataset
uspto-grants-1994_01
Patent number
US05280039

Reaction notes

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