Hydroquinone → HCID 88834841, compound

HRID 1658520Notes

Reaction equation

HRID 1658520 reaction equation
[ClH:1].[CH2:2]([N:9]1[CH2:14][CH:13]=[C:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH:27]=[CH:26]1.C(OC(=O)C)(=O)C.C1(C=CC(O)=CC=1)O>C(O)(=O)C>[ClH:1].[CH2:2]([N:9]1[CH2:10][CH2:11][C:12]2[CH:13]([CH:26]3[C:25](=[O:31])[O:30][C:28](=[O:29])[CH:27]3[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:15]=2)[CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 2837641HCID 2837641, compound

Product 1

HCID 88834841HCID 88834841, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 21 g (0.06 moles) 1-benzyl-1,2,3,6-tetrahydro-4-(p-methoxystyryl)-pyridine, hydrochloride, from example 6, 37.8 g ground maleic anhydride, 135 ml. glacial acetic acid, 135 ml. acetic anhydride and 20 mg hydroquinone is refluxed under nitrogen for 1/2 hour. The solution is allowed to cool and evaporate to an oil. The crude Diels-Alder adduct (quantitative yield of 2-benzyl-1,2,3,4,6,7,8,8a-octahydro-6-(p-methoxyphenyl)-7,8-isoquinoline-dicarboxylic acid anhydride hydrochloride) is dissolved in 500 ml. methanol and 20 ml. hydrochloric acid in isopropanol and refluxed for 18 hours. The solution is allowed to cool and evaporated. The residue is triturated in ether and solid filtered to afford a quantitative yield of 2-benzyl-1,2,3,4,6,7,8,8a-octahydro-6-(p-methoxyphenyl)-7,8-isoquinoline-dicarboxylic acid, dimethyl ester, hydrochloride. After recrystallization from acetone-ether the mp is 200° to 209°C with decomposition.

Workup

  1. temperatureto cool
  2. customevaporate to an oil

Sources & evidence

ORD record
ord-385a9100c7134d42ada293da4db2fcfc
Source dataset
uspto-grants-1976_06
Patent number
US03965102

Reaction notes

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