(2-Chlorobenzyl)triphenylphosphonium Chloride → 2-[2-(2-Chlorophenyl)ethenyl]-5-nitro-1H-indole

HRID 11162Notes

Reaction equation

HRID 11162 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH:13]=O)=[CH:7]2)([O-:3])=[O:2].[Cl-].[Cl:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[CH2:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>>[Cl:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[CH:19]=[CH:13][C:8]1[NH:9][C:10]2[C:6]([CH:7]=1)=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2

Participants

3

Reactant 2

HCID 2734112(2-Chlorobenzyl)triphenylphosphonium ChlorideHCID 219808825-Nitro-1H-indole-2-carbaldehyde

Product 1

HCID 695838952-[2-(2-Chlorophenyl)ethenyl]-5-nitro-1H-indole

Procedure

Reaction of the aldehyde (904) prepared as described in example 454 with 2-chlorobenzyltriphenylphosphonium chloride using the procedure described in example 37(at room temperature) gave the diene (905) as a mixture of E/Z isomers as a yellow solid (95%). Crystallisation from aqueous methanol yielded the pure E-isomer as yellow needles (80%), mp 230–232° C. 1H NMR δ [(CD3)2SO] 12.28 (br s, 1H), 8.55 (d, J=2.3 Hz, 1H), 8.03 (dd, J=9.1, 2.3 Hz, 1H), 7.91 (dd, J=7.8, 1.5 Hz, 1H), 7.32–7.61 (m, 6H), 6.92 (s, 1H). Found: C, 64.59; H, 5.68; N, 9.49. C16H11ClN2O2 requires C, 64.33; H, 5.68; N, 9.49.

Workup

  1. customprepared
  2. customdescribed in example 37(at room temperature

Sources & evidence

ORD record
ord-e267445cc72d435f96613a64bd3211d4
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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