Methanol → Methyl (cis)-4-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydro-1H-phthalazin-2-ylmethyl)benzoate

HRID 1871418Notes

Reaction equation

HRID 1871418 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[C@H:24]3[C@H:19]([CH2:20][CH2:21][CH2:22][CH2:23]3)[C:18](=[O:25])[N:17]([CH2:26][C:27]3[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=3)[N:16]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].[CH3:36]O>>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[C@H:24]3[C@H:19]([CH2:20][CH2:21][CH2:22][CH2:23]3)[C:18](=[O:25])[N:17]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:31]([O:33][CH3:36])=[O:32])=[CH:34][CH:35]=3)[N:16]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86755615(cis)-4-(4-(3,4-Dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydro-1H-phthalazin-2-ylmethyl)-benzoic acid

Product 1

HCID 86755620Methyl (cis)-4-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydro-1H-phthalazin-2-ylmethyl)benzoate

Procedure

3 ml of thionyl chloride was added slowly to a solution of 1 g of compound 83 in methanol at -20° C. After complete addition, the mixture was stirred for 6 hours at room temperature and subsequently evaporated. The compound was crystallized from diethyl ether at -20° C. M.p. 90°-92° C.

Workup

  1. additionAfter complete addition
  2. customsubsequently evaporated
  3. customThe compound was crystallized from diethyl ether at -20° C

Sources & evidence

ORD record
ord-eac4296a2b5443dc997b76047dd01e7e
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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