Sulfuric Acid → HCID 86683410, compound

HRID 579434Notes

Reaction equation

HRID 579434 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH2:10]2)=[CH:5][C:4]=1[O:21][CH3:22])=[O:2].S(=O)(=O)(O)[OH:24].C([O-])([O-])=O.[K+].[K+]>>[CH:1]([C:3]1[C:4]([O:21][CH3:22])=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH2:10][N:9]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH2:18])=[O:24])=[CH:19][CH:20]=1)[CH2:8]2)=[O:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 86683411HCID 86683411, compound

Product 1

HCID 86683410HCID 86683410, compoundYield 39.7%

Procedure

A mixture of 4-(7-formyl-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-benzonitrile (200 mg, 0.68 mmol) and 96% (w/w) sulfuric acid (3 mL) was stirred at room temperature overnight. The next day poured onto ice-water (10 mL), the pH was adjusted with K2CO3 to 9 and the mixture was extracted with ethyl acetate. The residue was purified by column chromatography over silica, elating with a 95:5 mixture of chloroform and methanol. In this manner the title compound (85 mg, 0.27 mmol, 39.7%) was obtained as a solid.

Workup

  1. additionThe next day poured onto ice-water (10 mL)
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe residue was purified by column chromatography over silica
  4. additionelating with a 95:5 mixture of chloroform and methanol

Sources & evidence

ORD record
ord-a27b62d0e637468c94dc3db6b120b00b
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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