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

HRID 442724ノート

反応式

HRID 442724 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 110331762-(3-Bromobenzoyl)-3-hydroxypyridine収率 93.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bd561cee7e7048ebbdbcb919dd0dc032
出典データセット
uspto-grants-1999_04
特許番号
US05891895

反応ノート

読み込み中…