Ammonia → N-(6-Cyano-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 1289218Notes

Reaction equation

HRID 1289218 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1Br)[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].[CH3:15][N:16]1C(=O)CCC1.N>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:15]#[N:16])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 104000345-Acetamido-6-bromoindan

Product 1

HCID 10536029N-(6-Cyano-2,3-dihydro-1H-inden-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 5-acetamido-6-bromoindan (143 g), cuprous cyanide (65.5 g) and NMP (600 ml) was stirred and heated to 125° C. for 30 minutes. The mixture was cooled to ambient temperature and poured into a mixture of concentrated aqueous ammonia solution (specific gravity 0.88, 1 L) and ice (3 L). The mixture was stirred for 15 minutes. The precipitate was isolated and washed with water (3 L). A mixture of the solid so obtained and methylene chloride (2 L) was stirred at ambient temperature for 30 minutes. The mixture was filtered and the filtrate was dried (MgSO4) and evaporated. The residue was triturated under diethyl ether (1.5 L). There was thus obtained 5-acetamido-6-cyanoindan (104 g), m.p. 172° C.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringThe mixture was stirred for 15 minutes
  3. customThe precipitate was isolated
  4. washwashed with water (3 L)
  5. additionA mixture of the solid
  6. customso obtained
  7. filtrationThe mixture was filtered
  8. dry with materialthe filtrate was dried (MgSO4)
  9. customevaporated
  10. customThe residue was triturated under diethyl ether (1.5 L)

Sources & evidence

ORD record
ord-4960c6772bcb46289180afb0f3eeb4d3
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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