2-Amino-6-methylpyridine → 2-chloro-N-(6-methylpyridin-2-yl)-2-phenylacetamide

HRID 872362Notes

Reaction equation

HRID 872362 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[Cl:18][CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20](Cl)=[O:21]>C1COCC1>[Cl:18][CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20]([NH:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:21]

Participants

5

Reactant 3

HCID 157652-Amino-6-methylpyridineHCID 81531DiisopropylethylamineHCID 102902Chloro(phenyl)acetyl chloride

Product 1

HCID 431324952-chloro-N-(6-methylpyridin-2-yl)-2-phenylacetamideYield 124.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 6-methylpyridin-2-amine [CAS 1824-81-3] (5.22 g, 44.08 mmol) in 350 mL anhydrous THF was added diisopropylethylamine (15.36 mL, 88.16 mmol). Chloro(phenyl)acetyl chloride [CAS 2912-62-1] (10.0 g, 52.9 mmol) was added dropwise and the resulting mixture was stirred for 1 h while cooling was maintained. The mixture was partitioned between ethyl acetate and water and the organic phase was washed with brine. The organic phase was filtered through a Whatman filter and the volatile components were removed by the use of a rotary evaporator to give title compound (14.3 g) in ˜80% purity (LC-MS). The crude material was forwarded directly to the next step.

Workup

  1. temperaturewhile cooling
  2. temperaturewas maintained
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washthe organic phase was washed with brine
  5. filtrationThe organic phase was filtered through a Whatman
  6. filtrationfilter
  7. customthe volatile components were removed by the use of a rotary evaporator

Sources & evidence

ORD record
ord-1626ad616d404673a0c26db2359e8cf7
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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