N-[2-(dimethylamino)ethyl]-6-nitro-1H-indole-2-carboxamide → 6-Amino-1H-indole-2-carboxylic acid (2-dimethylamino-ethyl)-amide

HRID 1071811Notes

Reaction equation

HRID 1071811 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([N+:17]([O-])=O)[CH:11]=2)=[O:7]>C(O)C.C(OC(=O)C)C.[Pd]>[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([NH2:17])[CH:11]=2)=[O:7]

Participants

4

Reactant 1

HCID 85801420N-[2-(dimethylamino)ethyl]-6-nitro-1H-indole-2-carboxamide

Product 1

HCID 867597646-Amino-1H-indole-2-carboxylic acid (2-dimethylamino-ethyl)-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 82.9 mg (0.3 mmole) 125 in a mixture of ethanol/ethylacetate 1:1 10% Pd/C (40 mg) was added. The flask was flushed 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 solid 126 was used for the next step without purification

Workup

  1. additionwas added
  2. customThe flask was flushed 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
  6. customThe solid 126 was used for the next step without purification

Sources & evidence

ORD record
ord-0a32027934d040a7aa8d963634b79be9
Source dataset
uspto-grants-2005_06
Patent number
US06906103B2

Reaction notes

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