1-Naphthaldehyde → HCID 136247054, compound

HRID 2370077Notes

Reaction equation

HRID 2370077 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:12])=[C:7]([CH:11]=1)[C:8]([NH2:10])=[O:9].[C:13]1([CH:23]=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>>[CH3:1][O:2][C:3]1[CH:11]=[C:7]2[C:6](=[CH:5][CH:4]=1)[N:12]=[C:23]([C:13]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=1)[NH:10][C:8]2=[O:9]

Participants

3

Reactant 2

HCID 61951-NaphthaldehydeHCID 203382172-Amino-5-methoxybenzamide

Product 1

HCID 136247054HCID 136247054, compound

Procedure

Compound 17 was synthesized from 5-methoxy-2-aminobenzamide (9) (1.2 g, 7.3 mmol) and 1-naphthaldehyde (14) (1.1 g, 7.3 mmol): yield 1.5 g (70%); pale yellow needles; mp 174 to 175° C.; 1H NMR (DMSO-d6) δ 3.87 (3H, s, OCH3), 7.22-7.34 (2H, m, 2×ArH), 7.53-7.72 (5H, m, 5×ArH), 7.95-8.22 (3H, m, 3×ArH), 12.62 (1H, br s, NH) ppm; MS (ESI) m/z 302; Anal. (C19H14N2O2): C, H, N.

Sources & evidence

ORD record
ord-29acc710e27a4a1aa86f605498dcd8c2
Source dataset
uspto-grants-2014_04
Patent number
US08710064B2

Reaction notes

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