p-Toluenesulfonic acid → (cis)-4-(4-Methoxy-3-hydroxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1one

HRID 1871452Notes

Reaction equation

HRID 1871452 reaction equation
C1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[C@H:24]4[C@H:19]([CH2:20][CH:21]=[CH:22][CH2:23]4)[C:18](=[O:25])[N:17]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[N:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([C:15]2[C@H:24]3[C@H:19]([CH2:20][CH:21]=[CH:22][CH2:23]3)[C:18](=[O:25])[N:17]([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[N:16]=2)=[CH:8][C:7]=1[OH:6]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70002575(cis)-4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Product 1

HCID 70120964(cis)-4-(4-Methoxy-3-hydroxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.3 g of compound 21 and 2 g of p-toluenesulfonic acid in 15 ml of toluene was refluxed for 4 h. After cooling to room temperature, themixture was washed with aqueous sodium carbonate, the toluene solution was dried over magnesium sulfate and evaporated. Crystallization from diethyl ether/petroleum ether (60-80° C.). M.p. 142-144° C.

Workup

  1. washthemixture was washed with aqueous sodium carbonate
  2. dry with materialthe toluene solution was dried over magnesium sulfate
  3. customevaporated
  4. customCrystallization from diethyl ether/petroleum ether (60-80° C.)

Sources & evidence

ORD record
ord-60bd47dee38a4e45ace687d8f6ee846c
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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