HCID 20337419, compound → HCID 20337479, compound

HRID 1706256Notes

Reaction equation

HRID 1706256 reaction equation
[CH2:1]([Li])CCC.[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH:17]([CH3:27])[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:13][C:12]([CH3:29])([CH3:28])[C:11]1[CH2:30][CH2:31][CH2:32][C:33](=O)[C:10]2=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH:17]([CH3:27])[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:13][C:12]([CH3:28])([CH3:29])[C:11]1[CH2:30][CH2:31][CH2:32][C:33](=[CH2:1])[C:10]2=1

Participants

5

Reactant 2

HCID 20337419HCID 20337419, compoundHCID 178418339Butyllithium

Product 1

HCID 20337479HCID 20337479, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A 1 N ethereal solution of butyllithium (9 ml.) is added with stirring, under a nitrogen atmosphere to a suspension of 3.57 g. (10 mmoles) of methyltriphenylphosphonium bromide (prepared from methyl bromide and triphenylphosphine) in 50 ml. of ether. 5,6,7,8,9,10-Hexahydro-2-hydroxy-3-(1-methyl-4-phenylbutyl)-6,6-dimethyl-10-oxo-benzo[c]quinoline (600 mg., 1.5 mmoles) dissolved in 100 ml. of ether is added and the mixture is stirred for four hours then allowed to stand overnight at room temperature. Ether is distilled off as tetrahydrofuran is added until most of the ether is replaced. The mixture was then refluxed for six hours, cooled and worked-up as described in Part A of Example 42 to obtain the title compound.

Workup

  1. stirringthe mixture is stirred for four hours
  2. distillationEther is distilled off as tetrahydrofuran
  3. additionis added until most of the ether
  4. temperatureThe mixture was then refluxed for six hours
  5. temperaturecooled

Sources & evidence

ORD record
ord-cad08746bf69492097e922831dc792d1
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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