Hydrazine → 6-Fluoroisoquinoline-3-carbohydrazide

HRID 340882Notes

Reaction equation

HRID 340882 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([F:15])=[CH:10][CH:9]=2)=O.[NH2:16][NH2:17]>C(O)C>[F:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[N:6][C:5]([C:3]([NH:16][NH2:17])=[O:2])=[CH:14]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57947434Methyl 6-fluoroisoquinoline-3-carboxylate

Product 1

HCID 579481706-Fluoroisoquinoline-3-carbohydrazideYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-fluoro-isoquinoline-3-carboxylic acid methyl ester (27 g) and hydrazine (42 g, 10 equiv.) in ethanol (500 mL) was refluxed for 2 h. The reaction mixture was concentrated under high vacuum to remove hydrazine, and the resulting residue was triturated with ethanol (100 mL) to give 6-fluoro-isoquinoline-3-carboxylic acid hydrazide as a light yellow solid (22.8 g, 84%). LRMS (M+H+) m/z 206.1.

Workup

  1. concentrationThe reaction mixture was concentrated under high vacuum
  2. customto remove hydrazine
  3. customthe resulting residue was triturated with ethanol (100 mL)

Sources & evidence

ORD record
ord-383bdf35eb29407fb9d7b0d1a9506bd4
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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