2-Hydroxy-1-naphthaldehyde → 3-Hydroxy-2-naphthoic (2-hydroxy-1-naphthylmethylene) hydrazide

HRID 976057Notes

Reaction equation

HRID 976057 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=O.[OH:14][C:15]1[C:16]([C:25]([NH:27][NH2:28])=[O:26])=[CH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2>>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=[N:28][NH:27][C:25]([C:16]1[C:15]([OH:14])=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)=[O:26]

Participants

3

Reactant 2

HCID 128192-Hydroxy-1-naphthaldehydeHCID 726993-Hydroxy-2-naphthoic acid hydrazide

Product 1

HCID 11090263-Hydroxy-2-naphthoic (2-hydroxy-1-naphthylmethylene) hydrazideYield 97%

Procedure

Following the general procedure of Example 1, condensation of 2-Hydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide gave a white solid (97%): mp >300° C.; 1H NMR d 12.70 (s, 1 H), 12.25 (br s, 1 H), 11.37 (br s, 1 H); 9.58 (s, 1 H), 8.52 (s, 1 H), 8.33 (d, 1 H, J=8.7 Hz), 7.94 (d, 2 H, J=8.7 Hz), 7.89 (d, 1 H, J=8.1 Hz), 7.78 (d, 1 H, J=8.4 Hz), 7.58 (t, 1 H, J=7.6 Hz), 7.52 (t, 1 H, J=7.5 Hz), 7.41 (m, 2 H), 7.37 (s, 1 H), 7.25 (d, 1 H, J=9.0 Hz); 13C NMR d 163.05, 158.12, 153.88, 147.57, 135.94, 132.90, 131.68, 130.62, 128.90, 128.68, 128.33, 127.79, 127.73, 126.81, 125.85, 123.86, 123.54, 120.98, 119.84, 118.87, 110.62, 108.61; HRMS Calcd for C22H16N2O3 :356.1161, found 356.1151; Anal. (C22H16N2O3) C, H, N.

Sources & evidence

ORD record
ord-fc956165d72b40b2a875c564173e60a6
Source dataset
uspto-grants-1997_03
Patent number
US05610192

Reaction notes

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