Hydrochloric Acid → 5-Amino-2-chloro-isonicotinic acid

HRID 887703Notes

Reaction equation

HRID 887703 reaction equation
C(OC([NH:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]([Cl:18])=[N:11][CH:10]=1)=O)(C)(C)C.Cl>[OH-].[K+]>[NH2:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]([Cl:18])=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 105641445-tert-Butoxycarbonylamino-2-chloroisonicotinic acid

Product 1

HCID 227367915-Amino-2-chloro-isonicotinic acidYield 45%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 5-tert-butoxycarbonylamino-2-chloro-isonicotinic acid (2.46 g) in aqueous 2N potassium hydroxide solution (45 mL) was stirred at 90° C. for 5 hours. After cooling to room temperature, the solution was acidified by slow addition of 6N hydrochloric acid. The formed precipitate was filtered off, washed with water, MTB-ether and hexane and dried in vacuum to afford 700 mg of the title compound of the formula

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe formed precipitate was filtered off
  3. washwashed with water, MTB-ether and hexane
  4. customdried in vacuum

Sources & evidence

ORD record
ord-aea6dd8f69214293890b299e2e3fcaab
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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