Hydrochloric Acid → HCID 18176432, compound

HRID 651607Notes

Reaction equation

HRID 651607 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[NH:13]C(=O)C.Cl>CCO>[NH2:13][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH3:1])[C:9](=[O:12])[NH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10443297HCID 10443297, compound

Product 1

HCID 18176432HCID 18176432, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(7-Methyl-1-oxo-1,2-dihydro-isoquinolin-6-yl)-acetamide (0.366 g, 1.69 mmol) and conc. HCl (0.5 mL) is heated to reflux in EtOH (0.84 mL). After 6 hours, the mixture is concentrated to dryness, then diluted with water and basified using 1 N NaOH until pH is ca. 10. The aqueous solution is extracted with methylene chloride (4×50 mL) and the organic layers are combined and washed with brine, dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 3% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2 to give the title product (0.200 g, 1.15 mmol) as a white solid.

Workup

  1. concentrationthe mixture is concentrated to dryness
  2. additiondiluted with water
  3. extractionThe aqueous solution is extracted with methylene chloride (4×50 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by column chromatography
  9. washeluting with a gradient of 3% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d623e11b4bf04546807b318d730be695
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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