Methanol → HCID 68295008, compound

HRID 572474Notes

Reaction equation

HRID 572474 reaction equation
[OH:1]S(O)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[N:16]([CH3:25])[C:15]=2[CH:26]([O:29][Si](C)(C)C)[C:27]#N)[CH:10]=[CH:11][C:12]=1[F:13].[CH3:34][OH:35]>>[CH3:34][O:35][C:27](=[O:1])[CH:26]([C:15]1[N:16]([CH3:25])[C:17](=[O:24])[C:18]2[C:23]([C:14]=1[C:9]1[CH:10]=[CH:11][C:12]([F:13])=[C:7]([F:6])[CH:8]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:29]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 86700716HCID 86700716, compound

Product 1

HCID 68295008HCID 68295008, compoundYield 79%

Procedure

To a mixture of conc. H2SO4 (2.5 ml) and methanol (7.5 ml) was added [4-(3,4-Difluoro-phenyl)-2-methyl-1-oxo-1,2-dihydro-isoquinolin-3-y]-trimethylsilanyloxy-acetonitrile (580 mg, 1.45 mmol), after addition, the resultant mixture was stirred at reflux overnight under N2. TLC showed SM was consumed, diluted with EA, adjusted with saturated NaHCO3 to pH=8˜9, extracted with EA, the organic layers was dried over Na2SO4 and concentrated to dryness to afford crude product. (m=430 mg, yield=79%). LCMS: (10-80 AB—2MIN-E.M): Rt=1.021, purity=64%, M+1=360.

Workup

  1. additionafter addition
  2. temperatureat reflux overnight under N2
  3. customwas consumed
  4. additiondiluted with EA
  5. extractionextracted with EA
  6. dry with materialthe organic layers was dried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customto afford crude product

Sources & evidence

ORD record
ord-791a02559f55455691b86239c2376716
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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