Calcium Carbonate → 4-Amino-2,6-dimethyl-3-iodopyridine

HRID 2254886

반응식

HRID 2254886 반응식
I(Cl)(=O)=O.[I:5](Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.[NH2:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([CH3:28])[CH:22]=1.C(=O)([O-])[O-].[Ca+2]>ClCCl.CO>[NH2:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([CH3:28])[C:22]=1[I:5]

참가 물질

5

반응물 3

HCID 10112Calcium CarbonateHCID 770474-Amino-2,6-dimethylpyridineHCID 56924451Trimethylbenzylammonium Dichloroiodate

생성물 1

HCID 129999544-Amino-2,6-dimethyl-3-iodopyridine수율 61.6%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

Benzyltrimethylammonium dichloroiodate (6 g) was added to 4-amino-2,6-dimethylpyridine (2.1 g) and calcium carbonate (2.25 g) in dichloromethane/methanol (55 ml) (8:3 v/v) and the mixture was stirred for 16 hours. Solvent was removed by evaporation and the residue partitioned between 5% sodium metabisulphite solution and dichloromethane. The aqueous phase was separated and washed with dichloromethane. The aqueous phase was then basified with sodium carbonate and extracted with dichloromethane. The organic phase was washed with water, saturated sodium chloride solution and dried (MgSO4). Solvent was removed by evaporation and the residue purified by flash chromatography eluting with dichloromethane/methanol (9:1 v/v) to give 4-amino-2,6-dimethyl-3-iodopyridine (B) (1.7 g) as a light yellow solid, m.p. 103°-110° C.; NMR (CDCl3): 2.3(s,3H), 2.7(s,3H), 4.6(br s,2H), 6.3(s,1H); mass spectrum (chemical ionisation): 249 (M+H)+.

후처리

  1. customSolvent was removed by evaporation
  2. customthe residue partitioned between 5% sodium metabisulphite solution and dichloromethane
  3. customThe aqueous phase was separated
  4. washwashed with dichloromethane
  5. extractionextracted with dichloromethane
  6. washThe organic phase was washed with water, saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customSolvent was removed by evaporation
  9. customthe residue purified by flash chromatography
  10. washeluting with dichloromethane/methanol (9:1 v/v)

출처 및 근거

ORD 기록
ord-8999635297044fc28e53e277a1217eb5
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05236937

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