2-Naphthaleneacetic acid → HCID 131732521, compound

HRID 868845Notes

Reaction equation

HRID 868845 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12](O)=O.Cl.[NH2:16][NH2:17].C([O:20][C:21](=[O:30])[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)Br)C>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1=[N:16][N:17]([CH:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:21]([OH:20])=[O:30])[C:21](=[O:20])/[C:22](=[CH:24]/[CH3:25])/[C:12]/1=[CH:28]\[CH:27]=[CH2:26]

Participants

4

Reactant 3

HCID 113932-Naphthaleneacetic acidHCID 97780Ethyl bromophenylacetateHCID 115031Hydrazinium chloride

Product 1

HCID 131732521HCID 131732521, compound

Procedure

This is made in a analogous fashion to example 11 starting with 2-Naphthyl acetic acid, ring expansion with hydrazine hydrochloride, alkylation with Ethyl-alpha-bromophenylacetate, and saponification to give the title compound. 16.4% overall yield, LC/MS (M++1): 421.4.

Sources & evidence

ORD record
ord-6e1c6a30696349fda7a83a38651df6d4
Source dataset
uspto-grants-2015_03
Patent number
US08969348B2

Reaction notes

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