Ethanol → 5,8-Dimethoxy-3-[(propan-2-yl)amino]-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 616981Notes

Reaction equation

HRID 616981 reaction equation
[O:1]1[CH:11]2[CH:2]1[CH2:3][C:4]1[C:5]([O:14][CH3:15])=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[CH2:10]2.C(O)C.[CH:19]([NH2:22])([CH3:21])[CH3:20]>>[CH3:20][CH:19]([NH:22][C@@H:2]1[CH2:3][C:4]2[C:9](=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:5]=2[O:14][CH3:15])[CH2:10][C@H:11]1[OH:1])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 6363IsopropylamineHCID 123670031a,2,7,7a-Tetrahydro-3,6-dimethoxynaphth[2,3-b]oxirene

Product 1

HCID 1736485,8-Dimethoxy-3-[(propan-2-yl)amino]-1,2,3,4-tetrahydronaphthalen-2-ol

Procedure

A mixture of 10.3 g of 6,7-epoxy-5,6,7,8-tetrahydro-1,4-dimethoxynaphthalene in 50 ml of isopropylamine containing 2.93 ml of absolute ethanol is heated overnight in a small Parr bomb at 105° C ± 5° C (internal pressure = 75-100 psi). The cooled reaction mixture is concentrated in vacuo to 11.51 g of tan solid. Trituration with ether gives 10.1 g of material, melting point 141-144° C. Two recrystallizations from ethyl acetate give 7.0 g of trans-1,2,3,4-tetrahydro-3-[(1-methylethyl)amino]-5,8-dimethoxy-2-dimethoxy-2-naphthalenol, melting point 144°-145° C.

Workup

  1. temperatureis heated overnight in a small Parr bomb at 105° C ± 5° C (internal pressure = 75-100 psi)
  2. customThe cooled reaction mixture
  3. concentrationis concentrated in vacuo to 11.51 g of tan solid

Sources & evidence

ORD record
ord-523c0660a4334d07b9d082992546526c
Source dataset
uspto-grants-1978_02
Patent number
US04076843

Reaction notes

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