Hydrazine hydrate (1:1) → HCID 57476238, compound

HRID 504809Notes

Reaction equation

HRID 504809 reaction equation
[CH3:1][O:2][CH:3]([O:21][CH3:22])[CH:4]1[S:8][C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[N+:18]([O-])=O)=[N:6][CH2:5]1.O.NN>C(O)C.O1CCCC1.[C].[Pd]>[CH3:22][O:21][CH:3]([O:2][CH3:1])[CH:4]1[S:8][C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[NH2:18])=[N:6][CH2:5]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57476237HCID 57476237, compound

Product 1

HCID 57476238HCID 57476238, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-7-nitro-1H-indole (16.25 g) in ethanol (200 mL) and tetrahydrofuran (100 mL) was added 10% palladium carbon (50% containing water, 2 g) under nitrogen atmosphere, and hydrazine monohydrate (14.5 mL) was added dropwise at room temperature. The reaction mixture was stirred at 80° C. for 20 min, and allowed to cool to room temperature. The palladium carbon was removed by the filtration, and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (11.2 g, yield 76%) as yellow crystals from a fraction eluted with ethyl acetate-hexane (50:50, volume ratio). MS: 292 (MH+).

Workup

  1. temperatureto cool to room temperature
  2. customThe palladium carbon was removed by the filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-08727e0fdef142189cc81af607d41dc8
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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