Urea → 2-Hydroxy-5-[1-hydroxy-2-(isopropylamino)ethyl]benzeneacetonitrile

HRID 26213Notes

Reaction equation

[CH:1]([NH2:4])([CH3:3])[CH3:2].C1(NC(C)(C)C)C=CC=CC=1.NC(N)=O.C(NN[CH2:25][C:26]([C:28]1[CH:29]=[CH:30][C:31]([OH:37])=[C:32]([CH2:34][C:35]#[N:36])[CH:33]=1)=[O:27])(C)C>>[OH:37][C:31]1[CH:30]=[CH:29][C:28]([CH:26]([OH:27])[CH2:25][NH:4][CH:1]([CH3:3])[CH3:2])=[CH:33][C:32]=1[CH2:34][C:35]#[N:36]

Participants

Reactant 4

HCID 1176Urea

HCID 6363Isopropylamine

HCID 254260N-(1,1-Dimethylethyl)benzenamine

HCID 213251615-[N-(isopropylamino)glycyl]-2-hydroxyphenylacetonitrile

Product 1

HCID 213251502-Hydroxy-5-[1-hydroxy-2-(isopropylamino)ethyl]benzeneacetonitrile

Procedure

The procedure of Example 1(c) is repeated with substitution of an equimolar amount of isopropylamine for phenyl-t-butylamine in that example. The resulting aminoketone, 5-[N-(isopropylamino)glycyl]-2-hydroxyphenylacetonitrile, is reduced according to the procedure of Example 1(d) to yield 2-hydroxy-5-[1-hydroxy-2-(isopropylamino)ethyl]benzeneacetonitrile.

Sources & evidence

ORD record: ord-c920c1946cc3415f81f3eb5e507834fe
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04148908

Reaction notes

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