Hydrochloric Acid → HCID 19806567, compound

HRID 1681391Notes

Reaction equation

HRID 1681391 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#N)=[CH:6][C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[CH:4][C:3]=1[CH3:16].[H-].C([Al+]CC(C)C)C(C)C.Cl.C(=O)(O)[O-:29].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[CH:6][C:7]=1[CH:8]=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 19806556HCID 19806556, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19806567HCID 19806567, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-amino-3-cyano-5-(4-methylimidazol-1-yl)toluene (166 mg) in tetrahydrofuran (2.6 ml) was added 1.5M diisobutylaluminium hydride (1.1 ml) at 0° C. and the mixture was stirred at 40° C. for 6 hours. After the reaction was completed, 10 ml of 3N hydrogen chloride solution was added to the reaction mixture. The whole mixture was stirred for 1 hour. The mixture was bacidified with saturated sodium bicarbonate solution and was extracted with chloroform. The extract was dried with Na2SO4 and solvent was distilled to give 63 mg (38%) of the title compound.

Workup

  1. stirringThe whole mixture was stirred for 1 hour
  2. extractionwas extracted with chloroform
  3. dry with materialThe extract was dried with Na2SO4 and solvent
  4. distillationwas distilled

Sources & evidence

ORD record
ord-40074c4fd66c4050b5923d3b44950317
Source dataset
uspto-grants-1992_12
Patent number
US05171851

Reaction notes

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