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

HRID 1604363Notes

Reaction equation

HRID 1604363 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 pH 5 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-6d06e7f8221c43f3acb633c7d9ad86ac
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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