Hydrochloric Acid → HCID 61609705, compound

HRID 1910688Notes

Reaction equation

HRID 1910688 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][CH:11]2[CH2:13][CH2:12]2)=C([CH:9]=1)C#N.[OH-:14].[K+].Cl.C1(C)C=CC=CC=1.[CH3:24][CH2:25][OH:26]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][CH:11]2[CH2:13][CH2:12]2)=[C:24]([CH:9]=1)[C:25]([OH:14])=[O:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1140TolueneHCID 14797Potassium HydroxideHCID 62494157HCID 62494157, compound

Product 1

HCID 61609705HCID 61609705, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Chloro-2-(cyclopropylamino)benzonitrile (4.66 g) was dissolved in a solution of KOH (4.75 g, 3.5 eq) in EtOH (12 mL) and water (2.5 mL). The solution was refluxed for 24 h, cooled, and acidified with concentrated HCl. The precipitate was filtered, washed with water, and dried by multiple concentrations from toluene delivering pure product (4.70 g, 92% yield). 1H-NMR (400 MHz, DMSO-d6) δ 7.88 (bs, 1H), 7.70 (d, 1H), 7.42 (dd, 1H), 7.09 (d, 1H), 2.47 (m, 1H), 0.78 (m, 2H), 0.45 (m, 2H).

Workup

  1. temperatureThe solution was refluxed for 24 h
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-4312f3a09a094b899151e2b6289e4bd2
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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