Acetic Anhydride → N-(2,3-Dihydro-1H-inden-2-yl)formamide

HRID 1761868Notes

Reaction equation

HRID 1761868 reaction equation
C(O[C:5](=[O:7])C)(=O)C.Cl.[NH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1.C([O-])(=O)C.[Na+]>C(O)=O>[CH:5]([NH:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)=[O:7]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 1227642-Aminoindan hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 14835235N-(2,3-Dihydro-1H-inden-2-yl)formamide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Acetic anhydride (40 ml) and formic acid (20 ml) were mixed and heated at 50° for 15 minutes with stirring. 2-Aminoindane hydrochloride (25 g) (see J. Med. Chem., 1980, 23, page 745) and sodium acetate (20 g) were added to this mixture which was then stirred at room temperature for 24 hours. The reaction mixture was poured into ice/water and extracted three times with methylene chloride. The combined organic layers were washed with water and aqueous sodium carbonate, dried (MgSO4) and evaporated in vacuo to give the title compound, yield 17.6 g, m.p. 72°-74°.

Workup

  1. temperatureheated at 50° for 15 minutes
  2. stirringwas then stirred at room temperature for 24 hours
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic layers were washed with water and aqueous sodium carbonate
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d94d974fd50549f19dafb663a42b72e0
Source dataset
uspto-grants-1989_05
Patent number
US04829071

Reaction notes

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