Hydrochloric Acid → 2-Amino-1(2H)-isoquinolinone

HRID 1680629Notes

Reaction equation

HRID 1680629 reaction equation
C1(C2C(=CC=CC=2)C=CO1)=O.O.NN.O.[NH2:16][N:17]1[CH:26](O)[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:28].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH2:16][N:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:28]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 68108IsocoumarinHCID 205530152-amino-3,4-dihydro-3-hydroxy-1H(2H)-isoquinolinone

Product 1

HCID 123832182-Amino-1(2H)-isoquinolinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of isocoumarin (26 g, 0.16 mol) in 95% ethanol (2000 ml) was treated with 25% hydrazine hydrate in water (64 ml, 0.32 mol) and stirred at room temperature for one hour. The precipitate of 2-amino-3,4-dihydro-3-hydroxy-1H(2H)-isoquinolinone was dissolved and dehydrated by addition of 10% hydrochloric acid (150 ml) at room temperature. After three hours, the mixture was neutralized with sodium carbonate and the ethanol recovered by distillation in vacuo. The title compound was isolated by filtration and extraction with chloroform to give 27.92 g (98%) of the product of the title. M.p. 103°-4° C.

Workup

  1. waitAfter three hours
  2. distillationthe ethanol recovered by distillation in vacuo

Sources & evidence

ORD record
ord-725ea9751ec74371975f32ecbadfc03b
Source dataset
uspto-grants-1981_06
Patent number
US04275066

Reaction notes

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