Phosphorus oxychloride → 6-Methoxy-1-thiophen-2-yl-3,4-dihydroisoquinoline

HRID 397050Notes

Reaction equation

HRID 397050 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=O)[CH:6]=[CH:7][CH:8]=1.P(Cl)(Cl)(Cl)=O>N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[C:12]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=[N:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 47222443Thiophene-2-carboxylic acid [2-(3-methoxyphenyl)ethyl]amide

Product 1

HCID 108002866-Methoxy-1-thiophen-2-yl-3,4-dihydroisoquinolineYield 110.1%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of thiophene-2-carboxylic acid [2-(3-methoxyphenyl)ethyl]amide (1.480 g, 5.66 mmol) in phosphorous oxychloride (10 ml, 107.3 mmol) was refluxed under N2 for 24 hr. The cooled reaction mixture was then slowly added to ice-water (50 ml) with stirring and basified to pH 10 with concentrated ammonia (60 ml). This was extracted with CHCl3 (4×25 ml) and the combined extracts were dried over MgSO4 then concentrated in vacuo to give 1.517 g (96% yield) of yellow oil.

Workup

  1. customThe cooled reaction mixture
  2. extractionThis was extracted with CHCl3 (4×25 ml)
  3. dry with materialthe combined extracts were dried over MgSO4
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-3b28af962a7d4730aa1a8d1a027f786b
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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