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

HRID 1829988Notes

Reaction equation

HRID 1829988 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-c68aed6a0408449ca9c064e7987ffd55
Source dataset
uspto-grants-2006_06
Patent number
US07064218B2

Reaction notes

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