Ammonium Hydroxide → 4-[(3-Amino-2-hydroxypropyl)oxy]benzonitrile

HRID 411146Notes

Reaction equation

HRID 411146 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[OH-].[NH4+:15]>C(O)(C)C>[NH2:15][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27643014-(2-Oxiranylmethoxy)benzenecarbonitrile

Product 1

HCID 167827394-[(3-Amino-2-hydroxypropyl)oxy]benzonitrileYield 46%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-(Oxiranylmethoxy)benzonitrile (from step (i) above; 100 g, 0.57 mol) was added to a mixture of concentrated aqueous ammonium hydroxide (500 mL) and iso-propanol (300 mL). The resulting slurry was stirred at room temperature for 3 days. The reaction mixture was filtered to remove the insoluble by-product, and the filtrate was concentrated in vacuo to give a crude product, which was crystallised from acetonitrile to yield 50 g (46%) of the sub-title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the insoluble by-product
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a crude product, which
  5. customwas crystallised from acetonitrile

Sources & evidence

ORD record
ord-79818506ad5d4c1890b05efb1fe2b899
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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