Pyridine → HCID 20361715, compound

HRID 1679668Notes

Reaction equation

HRID 1679668 reaction equation
N1C=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC([N:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][C:16]3[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=3[C:18]=2[NH2:22])[CH2:13]1)=O)C.S(OC)(OC)(=O)=O>O>[N:22]1([C:18]2[C:17]3[CH:23]=[CH:24][CH:25]=[CH:26][C:16]=3[CH:15]=[C:14]3[C:19]=2[CH2:20][CH2:21][NH:12][CH2:13]3)[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6497Dimethyl SulfateHCID 54308381HCID 54308381, compound

Product 1

HCID 20361715HCID 20361715, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3 ml of pyridine are added to a mixture of 27.0 g of 5-amino-1,2,3,4-tetrahydrobenzo[g]isoquinolin-2-ylcarboxylic acid ethyl ester in 50 ml of water. 50.4 g of dimethyl sulphate are added dropwise to this mixture within 10 minutes and the mixture is stirred for 8 hours at 55° - 60°. The resulting clear solution is diluted with 100 ml of water, and is extracted several times with chloroform. The extracts are washed neutral with water, are dried over sodium sulphate and concentrated by evaporation. The oily residue is taken up in ether, is made acid with ethereal hydrochloric acid solution and the precipitated product is filtered off and recrystallized from ethanol/ether. M.Pt. of 5-methylamino-1,2,3,4-tetrahydrobenzo[g]isoquinolin-2-ylcarboxylic acid ethyl ester hydrochloride 214° - 215°.

Workup

  1. extractionis extracted several times with chloroform
  2. washThe extracts are washed neutral with water
  3. dry with materialare dried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. filtrationthe precipitated product is filtered off
  6. customrecrystallized from ethanol/ether
  7. customof 5-methylamino-1,2,3,4-tetrahydrobenzo[g]isoquinolin-2-ylcarboxylic acid ethyl ester hydrochloride 214° - 215°

Sources & evidence

ORD record
ord-6a62024439c34e6faea3cd88b89bac9d
Source dataset
uspto-grants-1978_03
Patent number
US04081543

Reaction notes

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