Bromine → 6-Bromo-2,4-dimethylpyridin-3-amine

HRID 1811585Notes

Reaction equation

HRID 1811585 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.[Br:10]Br>C(Cl)Cl>[Br:10][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 149107812,4-Dimethylpyridin-3-amine

Product 1

HCID 288753476-Bromo-2,4-dimethylpyridin-3-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,4-dimethylpyridin-3-amine (2.0 g, 16 mmol) in CH2Cl2 (20 mL), was added a solution of bromine (3.16 g; 20 mmol) in CH2Cl2 (5 mL) at 0° C. for 5 min. The reaction was concentrated under vacuum. The reaction was poured into H2O (50 mL), extracted with CH2Cl2, washed with Na2SO3 solution, and dried over MgSO4. The CH2Cl2 was concentrated under vacuum to afford the crude compound. The crude was purified over SiO2 to afford to give 6-bromo-2,4-dimethylpyridin-3-amine. 1HNMR (CDCl3, 400 MHz) δ 2.10 (s, 3H), 2.31 (s, 3H), 4.85-5.10 (b, 2H), 7.05 (s, 1H). Exact mass calculated for C7H9BrN2 201.06. found 202.3 (MH+).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. additionThe reaction was poured into H2O (50 mL)
  3. extractionextracted with CH2Cl2
  4. washwashed with Na2SO3 solution
  5. dry with materialdried over MgSO4
  6. concentrationThe CH2Cl2 was concentrated under vacuum
  7. customto afford the crude compound
  8. customThe crude was purified over SiO2
  9. customto afford

Sources & evidence

ORD record
ord-2c4a5becfc7546ecb8a27cf100868a25
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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