1,2-Dichlorobenzene → HCID 21506608, compound

HRID 1287842Notes

Reaction equation

HRID 1287842 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12]Cl)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:19]([NH:21][CH2:22][C:23]#[N:24])=[O:20].ClC1C=CC=CC=1Cl.[Sn](Cl)(Cl)(Cl)Cl>O=[Pt]=O.CO>[CH3:31][O:30][C:26]1[CH:25]=[C:18]([CH:17]=[C:16]([O:15][CH3:14])[C:27]=1[O:28][CH3:29])[C:19]([NH:21][CH2:22][CH:23]1[C:6]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=2)[CH2:11][CH2:12][NH:24]1)=[O:20]

Participants

7

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 24287Tin tetrachlorideHCID 1811373HCID 1811373, compoundHCID 30153594-(2-Chloroethyl)-1,2-dimethoxybenzene

Product 1

HCID 21506608HCID 21506608, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.0 g. of 1-(3,4-dimethoxyphenyl)-2-chloroethane and 2.5 g of 3,4,5-trimethoxybenzamidoacetonitrile (obtainable from aminoacetonitrile and 3,4,5-trimethoxybenzoyl chloride) is allowed to stand overnight at 20° in 100 ml. of o-dichlorobenzene and with 2.6 g. of tin tetrachloride; the mixture is thereafter heated for 3 hours to 110°. The solution is concentrated by evaporation, and the residue is shaken with chloroform and sodium hydroxide solution. The chloroform solution is evaporated, and the thus-obtained crude 1-(3,4,5-trimethoxybenzamidomethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline is dissolved in 30 ml. of methanol and hydrogenated with 200 mg. of PtO2 at 20° and under normal pressure. After filtration, evaporation, and purification by chromatography on silica gel, 1-(3,4,5-trimethoxybenzamidomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline is obtained; hydrochloride, m.p. 234°-236°.

Workup

  1. additionA mixture of 2.0 g
  2. temperaturethe mixture is thereafter heated for 3 hours to 110°
  3. concentrationThe solution is concentrated by evaporation
  4. customThe chloroform solution is evaporated
  5. customthe thus-obtained crude 1-(3,4,5-trimethoxybenzamidomethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline
  6. dissolutionis dissolved in 30 ml
  7. customat 20°
  8. filtrationAfter filtration, evaporation, and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-7b43437f51eb40969e7823ec541fd4a7
Source dataset
uspto-grants-1976_10
Patent number
US03985881

Reaction notes

Loading…