Hydrazine → Isoquinoline-6-carbohydrazide

HRID 598812Notes

Reaction equation

HRID 598812 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:26][NH2:27]>CN(C=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:26][NH2:27])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 682631,1'-CarbonyldiimidazoleHCID 22128831Isoquinoline-6-carboxylic acid

Product 1

HCID 57950576Isoquinoline-6-carbohydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Isoquinoline-6-carboxylic acid (1.2 g, 6.94 mmol) purchased from Gateway Chemical Technology, Inc. was mixed with CDI (1.68 g, 10.4 mmol) in DMF (20 Ml) in a round bottom flask. After the mixture was stirred for 30 minutes at 20° C., anhydrous hydrazine (2 mL) was added and the resulting mixture was stirred at 20° C. for one hour. After removing the solvent at a reduced pressure, the remaining residue was mixed with 20 mL water. After filtration, washing with water and air drying, an off-white solid was obtained as the desired product. LCMS (API-ES) m/z (%): 188.0 (100%, M++H).

Workup

  1. stirringthe resulting mixture was stirred at 20° C. for one hour
  2. customAfter removing the solvent at a reduced pressure
  3. additionthe remaining residue was mixed with 20 mL water
  4. filtrationAfter filtration
  5. washwashing with water and air
  6. customdrying

Sources & evidence

ORD record
ord-55c380eacdff4aaea03c23bddcb993d3
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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