1-Naphthalenemethanamine → 3-[(Naphthalene-1-ylmethyl)amino]pyridine-4-carboxylic acid

HRID 63059

Reaction equation

HRID 63059 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.F[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>>[C:1]1([CH2:11][NH:12][C:19]2[CH:20]=[N:21][CH:22]=[CH:14][C:15]=2[C:16]([OH:18])=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 83551-NaphthalenemethanamineHCID 3453613-Fluoropyridine-4-carboxylic acid

Product 1

HCID 771057053-[(Naphthalene-1-ylmethyl)amino]pyridine-4-carboxylic acidYield 66%

Procedure

The title compound was prepared in 66% yield from 1-naphthylmethylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 13.39 (br s, 1H), 8.25 (s, 1H), 8.15 (d, 1H, J=7.9 Hz), 7.98 (d, 1H, J=7.5 Hz), 7.84-7.89 (m, 2H), 7.45-7.62 (m, 5H), 5.03 (s, 2H). [M+H] calc'd for C17H14N2O2, 279. found 279.

Sources & evidence

ORD record
ord-d36edc9b096344d9981868c7ada7b1b2
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Linked notes

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