Ethylamine → 6-(Ethylamino)pyridine-3-carboxylic acid

HRID 1870753Notes

Reaction equation

HRID 1870753 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH2:11]([NH2:13])[CH3:12]>>[CH2:11]([NH:13][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)[CH3:12]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 792226-Chloronicotinic acid

Product 1

HCID 117449946-(Ethylamino)pyridine-3-carboxylic acidYield 84%

Conditions

Temperature
170 °C

Procedure

6-Chloronicotinic acid (100 g, 0.63 mol) was treated with ethylamine (70% in water, 500 ml). The reaction was sealed in an autoclave and heated to 170° C. for 6 hours. The reaction mixture was evaporated, partially neutralised with concentrated HCl and the pH adjusted to pH5 with glacial acetic acid. The solid product was filtered off and dried in vacuo for 18 hours to give 6-(ethylamino)nicotinic acid (87.8 g, 84%).

Workup

  1. customThe reaction was sealed in an autoclave
  2. customThe reaction mixture was evaporated
  3. filtrationThe solid product was filtered off
  4. customdried in vacuo for 18 hours

Sources & evidence

ORD record
ord-224414ca27814aaeafbc4bcbbed3dc60
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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