Ammonia → 6-Amino-5-nitronicotinic acid

HRID 2368654Notes

Reaction equation

HRID 2368654 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[NH3:14]>>[NH2:14][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 3464596-Chloro-5-nitropyridine-3-carboxylic acid

Product 1

HCID 2718816-Amino-5-nitronicotinic acid

Procedure

6-Chloro-5-nitro-nicotinic acid (3.00 g, 14.8 mmol) in 100 mL conc. ammonia was stirred for 16 h. The mixture was concentrated, the residue mixed with 50 mL water, acidified with hydrochloric acid and stirred for 10 min. The precipitate was filtered off and washed with water. The solid was dried and taken up in refluxing THF. The mixture was filtered and concentrated. The residue was reacted without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue mixed with 50 mL water
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customThe solid was dried
  6. temperaturein refluxing THF
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated
  9. customThe residue was reacted without further purification

Sources & evidence

ORD record
ord-a2b986d8eb664b03b46faf47e60cf01e
Source dataset
uspto-grants-2014_04
Patent number
US08703796B2

Reaction notes

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