2-(Chloromethyl)anisole → (cis)-4-(3,4-Dimethoxyphenyl)-2-(2-methoxybenzyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

HRID 1871412Notes

Reaction equation

HRID 1871412 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[O:21])[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Cl.C(N1N=C(C2C=CC(OC)=C(OC)C=2)[C@H]2[C@H](CCCC2)C1=O)C1C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C@H:20]3[C@H:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[O:21])[N:13]([CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[O:23][CH3:22])[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 814952-(Chloromethyl)anisoleHCID 10913208(cis)-4-(3,4-Dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-oneHCID 70001660(cis)-2-Benzyl-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

Product 1

HCID 70002227(cis)-4-(3,4-Dimethoxyphenyl)-2-(2-methoxybenzyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

Procedure

Prepared from compound 1 and 2-methoxybenzylchloride as described for compound 78. Purified by chromatography (dichloromethane). Crystallized from diethyl ether at -20° C. M.p. 96°-99° C.

Workup

  1. customPurified by chromatography (dichloromethane)
  2. customCrystallized from diethyl ether at -20° C

Sources & evidence

ORD record
ord-7add78c7a8c846a8940503b2cd316c79
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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