Hydrochloric Acid → N-(6-Chloropyridin-2-yl)-2,2-dimethylpropanamide

HRID 1943129Notes

Reaction equation

HRID 1943129 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 13154248N-(6-Chloropyridin-2-yl)-2,2-dimethylpropanamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 6-chloro-2-pyridinamine (13.776 g, 107 mmol) in toluene (100 ml) and triethylamine (16.28 ml, 118 mmol) at 50° C. under argon was treated with 2,2-dimethylpropanoyl chloride (13.81 ml, 112 mmol). The reaction was then stirred at 50° C. for 4 h and then at rt for 18 h. 2M HCl (200 ml) was then added and the mixture was extracted with diethyl ether (3×500 ml). The organic extracts were dried (MgSO4), filtered and evaporated to give the product as a brown solid (21.005 g, 92%).

Workup

  1. waitat rt for 18 h
  2. extractionthe mixture was extracted with diethyl ether (3×500 ml)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9d1d98d621174096b76baf02fcbc7c17
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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