Anthranilic Acid → 2-[(4-Methoxy-naphthalen-1-ylmethyl)-amino]-benzoic acid

HRID 1663070Notes

Reaction equation

[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=O)=[CH:15][CH:14]=1>>[CH3:11][O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[CH:15][CH:14]=1

Participants

Reactant 2

HCID 227Anthranilic Acid

HCID 852174-Methoxy-1-naphthaldehyde

Product 1

HCID 589899912-[(4-Methoxy-naphthalen-1-ylmethyl)-amino]-benzoic acid

Procedure

Prepared by a similar procedure as described for preparation 1A, starting from anthranilic acid and 4-methoxy-1-naphthaldehyde (Aldrich). 13C-NMR (DMSO-d6) δ 169.9, 154.4, 150.7, 134.4, 131.8, 131.6, 126.7, 125.8, 125.7, 125.2, 125.1, 123.3, 122.0, 114.4, 111.6, 110.1, 103.7, 55.4, 43.9.

Workup

customPrepared by a similar procedure

Sources & evidence

ORD record: ord-fb6f60687353478c897c4602f8dbf324
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034811B2

Reaction notes

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