(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate → Methyl indole-6-carboxylate

HRID 330135

Reaction equation

HRID 330135 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-])=O>O1CCCC1.[Pd]>[NH:15]1[C:6]2[C:5](=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]=2)[CH:4]=[CH:3]1

Participants

4

Reactant 1

HCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

Product 1

HCID 639844Methyl indole-6-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (5.58 g) in tetrahydrofuran (100 ml) was hydrogenated at 3.45 bar in the presence of 10% (w/w) palladium on carbon (1.1 g) for 35 min. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated. The residue was dissolved in ethyl acetate and the solution obtained was washed successively with 10% (v/v) hydrochloric acid, water, and brine; then dried (MgSO4) and evaporated to give methyl indole-6-carboxylate (3.32 g, 85%) as a white solid; NMR (80 MHz, CDCl3): 3.92(s, 3H, OCH3), 6.57(m, 1H, H3 -indole), 7.32(t, 1H, H2 -indole), 7.10(d, 1H, H4 -indole), 7.87(dd, 1H, H5 -indole), 8.16(broad s, 1H, H7 -indole).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customthe solution obtained
  5. washwas washed successively with 10% (v/v) hydrochloric acid, water, and brine
  6. dry with materialthen dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-c851ade32e1545e3b774a6e2b945221d
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Linked notes

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