Toluene → HCID 54448452, compound

HRID 1683774Notes

Reaction equation

HRID 1683774 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([CH:14]=O)=[CH:4][CH:3]=1.C1(P(=CC=[O:37])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]1(C)C=C[CH:41]=[CH:40][CH:39]=1>>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([CH:14]=[CH:38][CH:39]=[CH:40][CH:41]=[O:37])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 19040638HCID 19040638, compound

Product 1

HCID 54448452HCID 54448452, compound

Conditions

Temperature
100 °C

Procedure

A solution of 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine-6-carboxaldehyde, prepared as in Example 12, (2.2 g, 10 mmol) in toluene (15 ml) was treated with triphenylphosphoranylideneacetaldehyde (4.4 g, 14 mmol) and stirred at 100° C. for 24 hours. The mixture was concentrated and the residue was triturated with ethyl ether-petroleum ether (4:1) and the supernatant concentrated to give 3 g of 5-(9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepin-6-yl)-2,4-pentadienal.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with ethyl ether-petroleum ether (4:1)
  3. concentrationthe supernatant concentrated

Sources & evidence

ORD record
ord-79b2375bfb934b26a1451575f0f224d8
Source dataset
uspto-grants-1997_06
Patent number
US05639748

Reaction notes

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