Dimethylamine → HCID 68681447, compound

HRID 1865479Notes

Reaction equation

HRID 1865479 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([CH3:20])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>>[CH3:1][N:2]([CH3:3])[C:5]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([CH3:20])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 18374283HCID 18374283, compound

Product 1

HCID 68681447HCID 68681447, compound

Procedure

A solution of dimethylamine (5 mL of 2M in THF) was added to ethyl 2-chloro-4-methyl-6-(trifluoromethyl)nicotinate (500 mg, 1.9 mmol) and stirred in a sealed tube for 24 hours. The mixture was partitioned between ethyl acetate (30 mL) and water (30 mL). The organic phase was dried over magnesium sulphate, filtered and evaporated to give ethyl 2-(dimethylamino)-4-methyl-6-(trifluoromethyl)nicotinate as a colourless oil (450 mg): 1H NMR (500 MHz, CDCl3): δ 6.79 (1H, s), 4.39 (2H, q, J 7.1), 3.05 (6H, s), 2.32 (3H, s), 1.39 (3H, t, J 7.1).

Workup

  1. customThe mixture was partitioned between ethyl acetate (30 mL) and water (30 mL)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-19e7d0b02b1a43698ac82b845da02067
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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