4-Pyridinecarboxaldehyde → 2-Methyl-6-[(pyridin-4-ylmethyl)-amino]-benzoic acid

Reaction equation

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

Participants

Reactant 2

HCID 133894-Pyridinecarboxaldehyde

HCID 1512106-Methylanthranilic acid

Product 1

HCID 589899552-Methyl-6-[(pyridin-4-ylmethyl)-amino]-benzoic acid

Procedure

Prepared by a similar procedure as described for preparation 1A, starting from 2-amino-6-methylbenzoic acid (Fluka) and pyridine-4-carbaldehyde. 13C-NMR (DMSO-d6) δ 170.4, 149.5, 149.3, 147.8, 138.5, 131.2, 121.9, 118.7, 115.8, 109.1, 45.1, 22.1.

Workup

customPrepared by a similar procedure

Sources & evidence

ORD record: ord-3ec030e59012453fbc61acb069187444
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034811B2

Reaction notes

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