Hydrochloric Acid → 2-Chloro-5-(3,4-dimethoxybenzoyl)pyridine

HRID 1031498노트

반응식

HRID 1031498 반응식
[Mg].Br[C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1.COC1C=C([Mg]Br)C=CC=1OC.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][N:27]=1.Cl>O1CCCC1>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](=[O:31])[C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([O:11][CH3:12])[CH:4]=2)=[CH:28][N:27]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 27821656-Chloronicotinoyl ChlorideHCID 5462224MagnesiumHCID 178491916HCID 178491916, 화합물

생성물 1

HCID 148232212-Chloro-5-(3,4-dimethoxybenzoyl)pyridine수율 67.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To 200 ml of tetrahydrofuran were added metallic magnesium (5.35 g) and 4-bromoveratrole (47.8 g), and the mixture was heated for 3 hours under reflux to prepare a 3,4-dimethoxyphenyl magnesium bromide solution. This solution was added, while stirring, dropwise at temperatures ranging from -50° C. to -60° C. to a solution of 6-chloronicotinic acid chloride (21.2 g) in tetrahydrofuran (200 ml) (the time required for the addition: one hour). The resultant mixture was stirred at the same temperature for 2 hours and 40 minutes, and there was then added 2N hydrochloric acid (100 ml). Precipitating crystals were collected by filtration, washed with water and dried to afford 2-chloro-5-(3,4-dimethoxybenzoyl)pyridine (22.5 g), m.p. 158° to 159° C.

후처리

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. additionThis solution was added
  4. additionrequired for the addition
  5. customone hour
  6. customPrecipitating crystals
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-08caf5d4817b4389807aea87041433cf
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04954497

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