Triethyl phosphite → 1,6-Dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 514787Notes

Reaction equation

HRID 514787 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH2:13][C:14]2=[O:19])([O-])=O.C(OP(OCC)OCC)C>>[CH2:12]1[C:11]2[C:10]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[NH:1][C:18]=3[CH:17]=[CH:16][C:15]=2[C:14](=[O:19])[CH2:13]1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 585449044-(2-Nitrophenyl)indan-1-one

Product 1

HCID 585448961,6-Dihydrocyclopenta[c]carbazol-3(2H)-oneYield 51.7%

Conditions

Temperature
120 °C

Procedure

Biphenyl 89 (9 g, 35 mmol) and triethylphosphite were added to a sealed bomb and heated at 120° C. overnight. After cooling to room temperature, the mixture was filtered to give 4 g of 1,2-dihydro-6H-cyclopenta[c]carbazole-3-one. Precipitation with diethyl ether yielded an additional 2 g of desired product. Common yield 90 as yellow powder was 77.5%.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-2241bacd9c3e4337932bcec086b90480
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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