Ethyl bromoacetate → HCID 18322352, compound

HRID 2254382Notes

Reaction equation

HRID 2254382 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([NH:12][CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH2:9]2)=[CH:4][CH:3]=1.OC1C=C2C(CCC(NCC(C3C=CC=C(Cl)C=3)O)C2)=CC=1.Br[CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47]>>[C:46]([CH2:45][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([NH:12][CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[OH:15])[CH2:9]2)=[CH:4][CH:3]=1)([O:48][CH2:49][CH3:50])=[O:47]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 129948HCID 129948, compoundHCID 129953HCID 129953, compound

Product 1

HCID 18322352HCID 18322352, compound

Procedure

Among the preparative methods of the products of formula (A) hereinabove, an O-alkylation is described that, starting from 2-[(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol or from 2-[(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-(3-chlorophenyl)ethanol, by reaction with ethyl bromoacetate gives the 2-[(7-carbethoxymethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-1-phenylethanol or the 2-[(7-carbethoxymethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-1-(3-chlorophenyl)ethanol. This reaction does not actually give good results because the yield in end product is very low.

Sources & evidence

ORD record
ord-ec895d6090f040528fdcc3be7e8e32b0
Source dataset
uspto-grants-1993_08
Patent number
US05235103

Reaction notes

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