Sulfuric Acid → HCID 86619220, compound

HRID 1788338Notes

Reaction equation

HRID 1788338 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]#N)[CH:7]=[CH:6]2.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S(=O)(=O)(O)[OH:28]>C1(C)C=CC=CC=1>[CH:13]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([NH:2][CH3:1])[CH:12]=[CH:11]2)=[O:28]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 68903420HCID 68903420, compound

Product 1

HCID 86619220HCID 86619220, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 6-methylamino-2-naphthonitrile (0.84 g, 4.6 mmol) prepared above in toluene (50 ml) was mixed with diisobutylaluminum hydride (9 ml, 1.0M (in toluene)) under a nitrogen atmosphere at −70° C. The mixture was stirred at −78° C. for 30 minutes and at room temperature for 4 hours. The mixture was added to a saturated solution of ammonium chloride, and then an aqueous solution of sulfuric acid was added thereto. The reaction mixture was extracted with ether, washed with brine, dried over MgSO4, and concentrated to give the title compound (0.76 g, yield: 89%).

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e260b1673e6470d921969f0b18aab52
Source dataset
uspto-grants-2009_03
Patent number
US07511167B2

Reaction notes

Loading…