Thioanisole → 952494-13-2

HRID 1690762Notes

Reaction equation

HRID 1690762 reaction equation
COC1C=C(C=CC=1OC)C[N:7]1[C:16]([CH3:18])([CH3:17])[CH:15]([C:19]([OH:21])=[O:20])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:22].C1(N2C(C)(C)C(C(O)=O)C3C(=CC=CC=3)C2=O)CC1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:17][C:16]1([CH3:18])[CH:15]([C:19]([OH:21])=[O:20])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:22])[NH:7]1

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 57781096HCID 57781096, compoundHCID 66906732HCID 66906732, compound

Product 1

HCID 57781109952494-13-2

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

To 2-(3,4-dimethoxy-benzyl)-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid (9.6 g, 26 mmol), prepared in manner analogous to 2-cyclopropyl-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid, is added thioanisole (36 mL, 304 mmol) and trifluoroacetic acid (360 mL). The resulting solution is heated to 70° C. for 13 h. The reaction is then cooled to room temperature and concentrated in vacuo to near dryness. The resulting purple oil is purified via silica gel flash chromatography (dichloromethane-methanol, 1:0 to 9:1, with 0.5% acetic acid) to furnish 3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid as an off-white foam; MS (ESI) m/z 220.0 (M+H).

Workup

  1. temperatureThe reaction is then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe resulting purple oil is purified via silica gel flash chromatography (dichloromethane-methanol, 1:0 to 9:1, with 0.5% acetic acid)

Sources & evidence

ORD record
ord-d1bcd449424545f88388baf012254d30
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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