Hydrochloric Acid → 2-Amino-4-hydroxythiophene-3-carbonitrile

HRID 1591282Notes

Reaction equation

HRID 1591282 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([O:10]CC)[C:7]=1[C:8]#[N:9].CO>O>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([OH:10])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 137423802-Amino-4-ethoxythiophene-3-carbonitrile

Product 1

HCID 135480882-Amino-4-hydroxythiophene-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 20 parts by volume of concentrated hydrochloric acid in 100 parts by volume of water is added dropwise to a boiling mixture of 168 parts of 2-amino-3-cyano-4-ethoxythiophene and 500 parts by volume of methanol. The mixture is refluxed for a further 2 hours and diluted with 400 parts by volume of water, and the product is filtered off under suction, washed with water and dried to give 136 parts of 2-amino-3-cyano-4-hydroxythiophene. The sample recrystallized from acetic acid does not melt below 300° C. and has the following analytical values:

Workup

  1. temperatureThe mixture is refluxed for a further 2 hours
  2. filtrationthe product is filtered off under suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c0c3e376905b4129b25d0bcb3d6a0f9a
Source dataset
uspto-grants-1993_04
Patent number
US05206375

Reaction notes

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