Anthranilic Acid → N-Phenylanthranilic Acid

Reaction equation

Br[C:2]1[CH:3]=[C:4](C)[CH:5]=[CH:6][C:7]=1[N+]([O-])=O.[NH2:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>>[C:2]1([NH:12][C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15]([OH:17])=[O:16])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 227Anthranilic Acid

HCID 81670382-Bromo-4-methyl-1-nitrobenzene

Product 1

HCID 4386N-Phenylanthranilic Acid

Procedure

As shown in Scheme 7, coupling of 3-bromo-4-nitrotoluene with 2-amino-benzoic acid via an Ullmann reaction yields an N-phenyl-anthranilic acid. After protection of the acid with 2-amino-2-methyl-1-propanol, oxidation affords the corresponding aldehyde. Addition of vinyl magnesium bromide and deprotection provides the N-phenyl-anthranilic acid containing a latent Michael acceptor. ##STR15##

Sources & evidence

ORD record: ord-b14e64830dbb4528bce163796757ab04
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258296

Reaction notes

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