N-bromobutanimide → 5-Bromo-6-cyclopropylpyridin-2-amine

HRID 531444Notes

Reaction equation

HRID 531444 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([NH2:10])[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[Br:11]N1C(=O)CCC1=O>CO>[Br:11][C:5]1[CH:6]=[CH:7][C:8]([NH2:10])=[N:9][C:4]=1[CH:1]1[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 457878636-Cyclopropylpyridin-2-amine

Product 1

HCID 900221395-Bromo-6-cyclopropylpyridin-2-amineYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-cyclopropylpyridin-2-amine (2 g, 14.93 mmol), methanol (25 mL) was added N-bromosuccinimide (2.64 g, 14.93 mmol) portionwise. After stirring at room temperature for 30 minutes, mixture was evaporated and the residue obtained was purified on column (SiO2) using 10% ethyl acetate in hexanes as eluent. This afforded 2.1 gm (68.5% yield) of title compound. 1H NMR (CDCl3, 300 MHz): δ 7.45-7.43 (d, 1H), 6.16-6.13 (d, 1H), 4.30-4.20 (bs, 2H), 2.40-2.30 (m, 1H), 1.00-0.90 (m, 2H), 0.85-0.80 (m, 2H). MS: m/z=215.0 (M+1).

Workup

  1. custommixture was evaporated
  2. customthe residue obtained
  3. customwas purified on column (SiO2)

Sources & evidence

ORD record
ord-b08bc7202e8243a7bcefec4157bcada5
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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