6-CHLORO-5-NITRONICOTINIC ACID → 5-Amino-6-chloropyridine-3-carboxylic acid

HRID 1277947Notes

Reaction equation

HRID 1277947 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[NH2:11][C:10]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 3464596-CHLORO-5-NITRONICOTINIC ACID

Product 1

HCID 204962365-Amino-6-chloropyridine-3-carboxylic acidYield 60%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 6-chloro-5-nitronicotinic acid in acetic acid (240 ml) was added iron (20 g) and the mixture was heated with stirring on a steam bath. After 11/2 hours, the mixture was filtered hot and washed with hot acetic acid. The filtrate was concentrated to dryness and the residue was treated with 10% NaOH, filtered and the pH adjusted to 2-3. The solid was filtered to yield 8.0 g (60% yield) of 5-amino-6-chloronicotinic acid.

Workup

  1. temperaturethe mixture was heated
  2. filtrationAfter 11/2 hours, the mixture was filtered hot
  3. washwashed with hot acetic acid
  4. concentrationThe filtrate was concentrated to dryness
  5. additionthe residue was treated with 10% NaOH
  6. filtrationfiltered
  7. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-a3289f514de64e9aaad3b598e675d697
Source dataset
uspto-grants-1981_07
Patent number
US04279913

Reaction notes

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