Diethyl Ether → 7-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid methyl ester hydrochloride

HRID 583241Notes

Reaction equation

HRID 583241 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:14][C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:20])=O.[CH3:22]COCC>CO>[ClH:20].[CH3:22][O:16][C:15](=[O:17])[CH2:14][CH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][NH:10]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 215842657-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid

Product 1

HCID 701156367-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid methyl ester hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 7-nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid (2.75 g, 11.5 mmol) in methanol (25 ml) at 0° C. was added dropwise thionyl chloride (3.6 ml, 41 mmol). After addition was complete, the reaction mixture was heated at reflux for 0.33 h. After cooling slightly, ether (50 ml) was added and the reaction mixture was cooled to 0° C. The precipitate was collected to give the title compound as a light yellow solid (3.09 g, 93%), m.p. 211-2° C.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 0.33 h
  4. temperatureAfter cooling slightly
  5. customThe precipitate was collected

Sources & evidence

ORD record
ord-ca8dec75be27466987a8d516c2ce6a48
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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