Acetone → 2-(3-Bromobenzoyl)-3-hydroxypyridine

HRID 442724노트

반응식

HRID 442724 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:12]([O:13]COC)=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].S(=O)(=O)(O)O.CC(C)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]

참가 물질

6

반응물 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 539766302-(3-Bromobenzoyl)-3-methoxymethoxypyridine

생성물 1

HCID 110331762-(3-Bromobenzoyl)-3-hydroxypyridine수율 93.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 2-(3-bromobenzoyl)-3-methoxymethoxy pyridine (5.55 g), 3.6N-sulfuric acid (11 mL) and acetone (30 mL) was subjected to reflux for 3 hours. The reaction mixture was poured into water, neutralized with an aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate) and then concentrated. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromobenzoyl)-3-hydroxypyridine (4.46 g) (compound C-1). Physical properties and spectrum date of the product are shown in Table 5 and Table 6. In substantially the same manner as above, compounds C-2 to C-4 and C-6 to C-9 shown in Table 5 were produced.

후처리

  1. temperatureto reflux for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

출처 및 근거

ORD 기록
ord-bd561cee7e7048ebbdbcb919dd0dc032
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891895

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