Ethanol → HCID 66713057, compound

HRID 523743Notes

Reaction equation

HRID 523743 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7](CC2C=CC(OC)=CC=2OC)[CH2:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:10]=2)=[O:5])[CH3:2].S(Cl)(Cl)=O.C(O)C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 66712780HCID 66712780, compound

Product 1

HCID 66713057HCID 66713057, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

365 mg of 2-(2,4-dimethoxy-benzyl)-4-hydroxy-7-phenoxy-1,2-dihydro-isoquinoline-3-carboxylic acid ethyl ester was dissolved in 7.9 ml of dichloromethane. To the solution was added 92 μL of thionyl chloride. The reaction was stirred at room temperature for 6.5 h, and then 500 μL of ethanol was added and the reaction stirred for an additional 10 min. The mixture was partitioned between ethyl acetate and sodium bicarbonate. The organic fraction was successively washed with 0.5 M HCl, water, brine; dried over anhydrous sodium sulfate, and concentrated to 468 mg of a yellow oil. The oil was purified by flash chromatography on silica gel, eluting with a gradient of 15-50% ethyl acetate in hexanes, to produce 232 mg of crude product, which was crystallized from ether and hexanes to give 193 mg of off-white solid; MS (+) m/z 310.08 (m+1).

Workup

  1. stirringthe reaction stirred for an additional 10 min
  2. customThe mixture was partitioned between ethyl acetate and sodium bicarbonate
  3. washThe organic fraction was successively washed with 0.5 M HCl, water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to 468 mg of a yellow oil
  6. customThe oil was purified by flash chromatography on silica gel
  7. washeluting with a gradient of 15-50% ethyl acetate in hexanes
  8. customto produce 232 mg of crude product, which
  9. customwas crystallized from ether and hexanes

Sources & evidence

ORD record
ord-1f2ccfc008fd46d997692f3b82d0cae3
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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