Hydrochloric Acid → HCID 577820, compound

HRID 2414941Notes

Reaction equation

HRID 2414941 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#N.[CH2:10]([Mg]Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.C([O:22]CC)C>>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4](=[O:22])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 729132-AminobenzonitrileHCID 178418336HCID 178418336, compound

Product 1

HCID 577820HCID 577820, compound

Procedure

A solution of 2-aminobenzonitrile (4.25 g, 36 mmol) in anhydrous diethyl ether (40 ml) at 0° C. is treated under argon with benzylmagnesium chloride (2M in tetrahydrofuran; 50 ml; 100 mmol). The reaction medium is maintained under agitation for 1 hour at ambient temperature, then hydrolyzed at 0° C. by adding hydrochloric acid at 10%, agitated for 1 hour, and neutralized with soda. The resulting mixture is extracted with ethyl acetate. The combined extracts are washed with water and with a saturated solution of sodium chloride, then dried over magnesium sulphate and concentrated to produce 3.5 g of the desired product, in the form of a white solid (m.p.: 100-101° C).

Workup

  1. customhydrolyzed at 0° C.
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washThe combined extracts are washed with water and with a saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76ca4682e42a4d088ec5291911f05da8
Source dataset
uspto-grants-2004_11
Patent number
US06815546B2

Reaction notes

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