Water → 2-Chloro-N-(6-methyl-3-pyridinyl)acetamide
Reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19].O>C1COCC1>[Cl:16][CH2:17][C:18]([NH:8][C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -60 °C
Procedure
A mixture of 6-methylpyridin-3-amine (1 g) and triethylamine (2.2 mL) in dry THF (20 mL) was stirred and cooled to −60° C. 2-Chloroacetyl chloride (1.567 g) was added via syringe to the stirred mixture forming a yellow suspension. The mixture was stirred at −60° C. until analysis showed complete disappearance of starting material. The reaction slurry was poured into water and the products extracted with ethyl acetate (2×150 ml). The combined organic extracts were dried over magnesium sulphate and concentrated to dryness. The crude brown solid was recrystallised from ether to afford the subtitled compound (700 mg).
Workup
- customforming a yellow suspension
- stirringThe mixture was stirred at −60° C. until analysis
- extractionthe products extracted with ethyl acetate (2×150 ml)
- dry with materialThe combined organic extracts were dried over magnesium sulphate
- concentrationconcentrated to dryness
- customThe crude brown solid was recrystallised from ether
Sources & evidence
- ORD record
- ord-347f5e37863c4d1eb26ac1a9c9c7e9dd
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329729B2
Reaction notes
Loading…