Chloroacetamide → methyl 9H-fluorene-9-carboxylate

HRID 485704Notes

Reaction equation

HRID 485704 reaction equation
Cl.CO.[Na].ClCC(N)=O.[CH3:10][O:11][C:12]([C:14]1(O)[C:26]2[CH:25]=[C:24](F)[CH:23]=[CH:22][C:21]=2[C:20]2[C:15]1=[CH:16][C:17](F)=[CH:18][CH:19]=2)=[O:13].[OH-].[Na+]>CO>[CH3:10][O:11][C:12]([CH:14]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:21]2[C:26]1=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:13]

Participants

7

Reactant 5

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

Product 1

HCID 232396methyl 9H-fluorene-9-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9H-fluoren-9-carboxylic acid methyl ester (19), which was prepared by refluxing 9-Hfluoren-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, 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.

Workup

  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%)

Sources & evidence

ORD record
ord-c25d419af844430bb0c01ca680b1887d
Source dataset
uspto-grants-1985_08
Patent number
US04537892

Reaction notes

Loading…