Triphenylphosphine → HCID 66665890, compound

HRID 522430Notes

Reaction equation

HRID 522430 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)([O-])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[C:20]([C:18]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]2[N:1]=[C:4]3[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]3)=[C:10]2[CH:19]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 66665571HCID 66665571, compound

Product 1

HCID 66665890HCID 66665890, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 15.3 g (50 mmol) of 2-(2-nitrophenyl)-4-tert-butylquinoline and 34.1 g (130 mmol) of triphenylphosphine in 150 ml of o-dichlorobenzene is heated under reflux for 12 h. After cooling, the solvent is removed in vacuo, the residue is recrystallised twice from ethyl acetate and then chromatographed on silica gel (DCM:heptane 3:1, v:v+0.2% of triethylamine). The solid obtained in this way is freed from readily volatile and non-volatile secondary components by fractional sublimation (p about 1×10−5 mbar, T about 180° C.). Yield: 8.8 g (32 mmol), 64%, purity: about 99.5% (NMR).

Workup

  1. temperatureunder reflux for 12 h
  2. temperatureAfter cooling
  3. customthe solvent is removed in vacuo
  4. customthe residue is recrystallised twice from ethyl acetate
  5. customchromatographed on silica gel (DCM:heptane 3:1, v:v+0.2% of triethylamine)
  6. customThe solid obtained in this way
  7. customby fractional sublimation (p about 1×10−5 mbar, T about 180° C.)

Sources & evidence

ORD record
ord-5062a126431c474eb56ea67b0ac2d919
Source dataset
uspto-grants-2016_05
Patent number
US09331290B2

Reaction notes

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