Sodium Hydroxide → 3,4-Dihydroisoquinoline

HRID 1828771Notes

Reaction equation

HRID 1828771 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]1([CH2:21][CH2:22][NH:23][CH:24]=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>O>[CH:24]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:21][CH2:22][N:23]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 140995Formamide, N-(2-phenylethyl)-

Product 1

HCID 767053,4-DihydroisoquinolineYield 74.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Polyphosphoric acid (25 g) and phosphorus pentoxide (5.4 g, 38.0 mmol) were heated to 180° C. over the course of one hour in an oil bath under an argon atmosphere. N-Phenylethylformamide (146) (4.3 g, 28.8 mmol) was then added at 160° C., and the mixture was stirred for 1.5 hours at constant temperature. The mixture was then allowed to cool to room temperature, and water (40 ml) was added. The mixture was subsequently adjusted to pH 10 by careful addition of saturated aqueous NaOH solution. The mixture was then extracted with ether (500 ml), and the organic phase was separated off and dried using NaOH. Evaporation gave a brown oil (2.81 g, 21.4 mmol, 74%).

Workup

  1. extractionThe mixture was then extracted with ether (500 ml)
  2. customthe organic phase was separated off
  3. customdried
  4. customEvaporation

Sources & evidence

ORD record
ord-d4d56fdf7e7f4d7ca3ed81f8977323e5
Source dataset
uspto-grants-2006_06
Patent number
US07060707B2

Reaction notes

Loading…