Water → N-((5-bromo-2-chloropyridin-4-yl)methylene)-2-methylpropan-2-amine

HRID 468778Notes

Reaction equation

HRID 468778 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([Cl:10])=[N:4][CH:3]=1.O.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>>[Br:1][C:2]1[C:7]([CH:8]=[N:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:5]([Cl:10])=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 534183815-Bromo-2-chloropyridine-4-carbaldehyde

Product 1

HCID 86674941N-((5-bromo-2-chloropyridin-4-yl)methylene)-2-methylpropan-2-amineYield 107.1%

Procedure

To a mixture of 5-bromo-2-chloroisonicotinaldehyde (1.047 g, 4.749 mmol) and Water (2.0 mL, 110 mmol) was added tert-butylamine (2.0 mL, 19 mmol). The reaction mixture was stirred at room temperature for 20 hours, and then excess tert-butylamine was removed by rotary evaporation. The resulting residue was partitioned between ethyl acetate and water, and the organic layer dried with brine and MgSO4, filtered, and evaporated in vacuo to yield 1.401 g (87%) of N-((5-bromo-2-chloropyridin-4-yl)methylene)-2-methylpropan-2-amine. 1H NMR (400 MHz, DMSO) δ 8.72 (s, 1H), 8.43 (s, 1H), 7.78 (s, 1H), 1.28 (s, 9H).

Workup

  1. customexcess tert-butylamine was removed by rotary evaporation
  2. customThe resulting residue was partitioned between ethyl acetate and water
  3. dry with materialthe organic layer dried with brine and MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-27e44d6a890d45e5829bd29ebc1a12cb
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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