Chloroacetamide → methyl 9H-fluorene-9-carboxylate

HRID 2413474노트

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HRID 2413474 반응식
C1C2C(C(O)=O)C3C(=CC=CC=3)C=2C=CC=1.Cl.CO.[Na].ClCC(N)=O.[CH3:26][O:27][C:28]([C:30]1(O)[C:42]2[CH:41]=[C:40](F)[CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][C:33](F)=[CH:34][CH:35]=2)=[O:29].[OH-].[Na+]>CO>[CH3:26][O:27][C:28]([CH:30]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=2[C:37]2[C:42]1=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:29]

참가 물질

8

반응물 6

HCID 6580ChloroacetamideHCID 14798Sodium HydroxideHCID 748099-CarboxyfluoreneHCID 5360545SodiumHCID 14075053Methyl 2,7-difluoro-9-hydroxy-9H-fluorene-9-carboxylateHCID 21893726Hydrochloride methanol

생성물 1

HCID 232396methyl 9H-fluorene-9-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

9H-fluoren-9-carboxylic acid methyl ester (19), which was prepared by refluxing 9H-fluoren-9-carboxylic acid (Aldrich Chemical, Inc.) in HCl/MeOH, (10.0 g, 44.6 mmol) was added to a solution of sodium (1.2 eq, 53.5 mmol, 1.23 g) in 100 mL methanol. After 15 min., 2-chloroacetamide (1.1 eq, 49.1 mmol, 4.59 g) was added and the mixture was allowed to stir at room temperature under nitrogen for two (2) days. The reaction mixture was poured into 400 mL of cold 2.5% w/v aqueous sodium hydroxide and the insoluble material was removed by filtration. The filtrate was chilled and acidified with concentrated hydrochloric acid to precipitate the spiro-succinimide which was collected and air dried to provide 6.7 g (60%). Recrystallization from methanol gave purified (20), 4.28 g (39%). m.p. 237°-239° C. Calc. %C 77.09, %H 4.45, %N 5.62: meas. %C 77.17, %H 4.55, %N 5.58.

후처리

  1. additionThe reaction mixture was poured into 400 mL of cold 2.5%
  2. customthe insoluble material was removed by filtration
  3. temperatureThe filtrate was chilled
  4. customto precipitate the spiro-succinimide which
  5. customwas collected
  6. customair dried
  7. customto provide 6.7 g (60%)
  8. customRecrystallization from methanol
  9. customgave
  10. custompurified (20), 4.28 g (39%)

출처 및 근거

ORD 기록
ord-60b5662776c14fb38ba21a45c2c764a4
출처 데이터셋
uspto-grants-1988_01
특허 번호
US04717725

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