Methyl 6-nitro-1H-indole-2-carboxylate → Methyl 6-amino-1H-indole-2-carboxylate

HRID 1071809Notes

Reaction equation

HRID 1071809 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([N+:14]([O-])=O)[CH:8]=2)=[O:4]>CO.C(OC(=O)C)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([NH2:14])[CH:8]=2)=[O:4]

Participants

4

Reactant 1

HCID 11816863Methyl 6-nitro-1H-indole-2-carboxylate

Product 1

HCID 22060206Methyl 6-amino-1H-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 6-Nitro-1H-indole-2-carboxylic acid methyl ester (108) 200 mg (0.91 mmole) in a mixture of methanol/ethylacetate 1:1 10% Pd/C (40 mg) was added. The flask was rinsed 3 times with hydrogen and filled with hydrogen at 30 to 35 psi. The suspension was stirred vigorously at room temperature for 30 minutes. The catalyst was filtered off, the filtrate was evaporated in vacuo to dryness. The resulted 6-amino-1H-indole-2-carboxylic acid methyl ester gave a single spot on TLC (Silica, toluene-ethylacetate 7:3, Rf: 0.31) and was used for the next step without purification

Workup

  1. additionwas added
  2. washThe flask was rinsed 3 times with hydrogen
  3. additionfilled with hydrogen at 30 to 35 psi
  4. filtrationThe catalyst was filtered off
  5. customthe filtrate was evaporated in vacuo to dryness

Sources & evidence

ORD record
ord-427a097925ef479eb9d0112eca9d3cb0
Source dataset
uspto-grants-2005_06
Patent number
US06906103B2

Reaction notes

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