Water → (cis)-4-(3-Ethoxy-4-methoxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

HRID 1871373Notes

Reaction equation

HRID 1871373 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]2[C@H:21]3[C@H:16]([CH2:17][CH:18]=[CH:19][CH2:20]3)[C:15](=[O:22])[NH:14][N:13]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:29](I)[CH3:30].O.CN1C[CH2:37][CH2:36][C:35]1=O>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]2[C@H:21]3[C@H:16]([CH2:17][CH:18]=[CH:19][CH2:20]3)[C:15](=[O:22])[N:14]([CH:30]3[CH2:29][CH2:37][CH2:36][CH2:35]3)[N:13]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 70003171(cis)-4-(3-Ethoxy-4-methoxyphenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Product 1

HCID 70303975(cis)-4-(3-Ethoxy-4-methoxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Procedure

A solution of 0.5 g of compound 6, 0.8 g of K2CO3 and 0.3 g of ethyliodide was stirred in 20 ml of N-methyl-pyrrolidinone for 4 h at 70° C. After cooling to room temperature, the reaction mixture was poured into 200 ml of water and this mixture was extracted with diethyl ether. After drying over magnesium sulfate, the solvent was evaporated and the compound crystallized from methanol, M.p. 124-127° C.

Workup

  1. extractionthis mixture was extracted with diethyl ether
  2. dry with materialAfter drying over magnesium sulfate
  3. customthe solvent was evaporated
  4. customthe compound crystallized from methanol, M.p. 124-127° C.

Sources & evidence

ORD record
ord-8d5af32f78cc457386501f9ef237bf0a
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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