Hydrazine → Diethyl Ether

HRID 2292752Notes

Reaction equation

HRID 2292752 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([CH3:19])=[C:6]2[CH2:20][C:21]([NH:23][NH2:24])=[O:22].[CH2:25]([O:27][C:28](=O)[CH2:29]C1C2C(=CC=C(OC)C=2)N(CC2C=CC=CC=2)C=1C)[CH3:26].NN>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([CH3:19])=[C:6]2[CH2:20][C:21]([NH:23][NH2:24])=[O:22].[CH3:26][CH2:25][O:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 10687376HCID 10687376, compoundHCID 10806873HCID 10806873, compound

Product 2

HCID 3283Diethyl EtherYield 96%HCID 10687376HCID 10687376, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide. A solution of 1.0 g (2.96 mmol) of 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester and 5 mL of hydrazine in 50 mL of MeOH was reacted as described in Example 3, Part C, to give by trituration with ether 920 mg (96% yield) of 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide mp, 161°-162° C.

Sources & evidence

ORD record
ord-33a77a6b17b04712893bb73be67ac932
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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