Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl 8-fluoroisoquinoline-3-carboxylate

HRID 2245285Notes

Reaction equation

HRID 2245285 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]([NH:19][C:20](=O)C)=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1C1OCCCO1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[CH3:1][O:2][C:3]([C:4]1[N:19]=[CH:20][C:7]2[C:6]([CH:5]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[F:12])=[O:23]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 685501862-Acetylamino-3-(2-[1,3]dioxan-2-yl-3-fluoro-phenyl)-acrylic acid methyl ester

Product 1

HCID 68551141Methyl 8-fluoroisoquinoline-3-carboxylateYield 75.8%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

2-Acetylamino-3-(2-[1,3]dioxan-2-yl-3-fluoro-phenyl)-acrylic acid methyl ester (10.6 g, 32.8 mmol) and pyridinium para-toluene sulfonate (2.06 g, 8.2 mmol) are heated to reflux for 20 hours in an acetone/water (120 ml/15 ml) mixture. The solvents are removed by evaporation and the aqueous residue is extracted with ethylacetate. The organic layer is washed with brine and dried over MgSO4 and evaporated. The crude product is recrystallised from ethylacetate/ether to afford 5.1 g of the desired compound. MS (ES+): m/e=206.2 (MH+)

Workup

  1. customThe solvents are removed by evaporation
  2. extractionthe aqueous residue is extracted with ethylacetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product is recrystallised from ethylacetate/ether

Sources & evidence

ORD record
ord-c5131429826b4ec5bfdc6155b181e35d
Source dataset
uspto-grants-2010_03
Patent number
US07683075B2

Reaction notes

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