Diethyl Ether → 8-Methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 1615044Notes

Reaction equation

HRID 1615044 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][C:13]3=[O:18])=[C:5]([N+:19]([O-])=O)[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C>ClC1C=CC=CC=1Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3[C:10]4[CH2:11][CH2:12][C:13](=[O:18])[C:14]=4[CH:15]=[CH:16][C:17]=3[NH:19][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 673683614-(4-Methoxy-2-nitrophenyl)indan-1-one

Product 1

HCID 709006108-Methoxy-1,6-dihydrocyclopenta[c]carbazol-3(2H)-oneYield 46%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(4-methoxy-2-nitrophenyl)-indan-1-one (81) (42 g, 148.4 mmol, 1 eq) and triphenylphosphine (116 g, 445 mmol, 3 eq) in o-dichlorobenzene (400 mL) was refluxed with vigorous stirring for 4 h, then cooled to 0° C. Diethyl ether (4 L) was added and the precipitate filtered off, washed with diethyl ether (3×100 mL) and dried to give 17 g (46%) of (82). The filtrate was evaporated out and the residue washed with cold MeOH (5×100 ml) to give an additional 10 g (27%) of the carbazole (82). Total yield 27 g (73%).

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed with diethyl ether (3×100 mL)
  3. customdried

Sources & evidence

ORD record
ord-8594672d3101467da8a1c1d6ae95f66a
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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