2-(3-Amino-2-hydroxypropoxy)benzonitrile → HCID 53711077, compound

HRID 729016Notes

Reaction equation

HRID 729016 reaction equation
[NH2:1][CH2:2][CH:3]([OH:14])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9].O=[CH:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CO>[C:8]([C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[O:5][CH2:4][CH:3]([OH:14])[CH2:2][N:1]=[CH:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:9]

Participants

4

Reactant 2

HCID 1931632-(3-Amino-2-hydroxypropoxy)benzonitrileHCID 110298063-Oxo-propionic acid ethyl ester

Product 1

HCID 53711077HCID 53711077, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In accordance with Example 10 above 2-(3-amino-2-hydroxypropoxy)benzonitrile was prepared. 1.9 g of this compound were dissolved in 30 ml of methanol and 1.16 g of ethyl 3-oxopropanoate were added, wereby ethyl N-[3-(2-cyanophenoxy)-2-hydroxypropyl]-3-iminopropanoate was obtained. Thesolution was cooled to 0° C. and at this temperature 3 g of sodium borohydride were added little by little, whereby the imino compound was reduced. The temperature was then allowed to rise to ambient temperature and after 1 hour 100 ml of H2O were added and the total mixture was extracted with ethyl acetate. The ethyl acetate phase was dried over MgSO4 and filtered. The residue was transformed into its hydrochloride. In this way ethyl N-[3-(2-cyanophenoxy)-2-hydroxypropyl]-3-aminopropanoate hydrochloride wasobtained. Melting point 120° C.

Sources & evidence

ORD record
ord-07592f368dbf41cbb24ecd6c985d0a9e
Source dataset
uspto-grants-1991_09
Patent number
US05051446

Reaction notes

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