3-Hydroxy-2-naphthoic acid hydrazide → HCID 136381079, compound

HRID 976062Notes

Reaction equation

HRID 976062 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[C:3]=1[CH:13]=O.[OH:15][C:16]1[C:17]([C:26]([NH:28][NH2:29])=[O:27])=[CH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2>>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[C:3]=1[CH:13]=[N:29][NH:28][C:26]([C:17]1[C:16]([OH:15])=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)=[O:27]

Participants

3

Reactant 2

HCID 726993-Hydroxy-2-naphthoic acid hydrazideHCID 116799472,6-dihydroxy-1-naphthaldehyde

Product 1

HCID 136381079HCID 136381079, compoundYield 72%

Procedure

Following the general procedure of Example 1, condensation of 2, 6-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded a yellow solid (72%): mp>280° C.; 1H NMR d 11.89 (s, 1 H), 11.75 (br s, 1 H), 10.90 (br s, 1 H), 9.14 (s, 1 H), 9.03 (s, 1 H), 8.06 (s, 1 H), 7.75 (d, 1 H, J=9.0 Hz), 7.48 (d, 1 H, J=8.4 Hz), 7.33 (d, 1 H, J=8.4 Hz), 7.28 (d, 1 H, J=9.0 Hz), 7.07 (t, 1 H, J=7.6 Hz), 6.92 (t, 1 H, J=7.4 Hz), 6.75-6.67 (m, 3 H), 6.90 (m, 2 H); 13C NMR d 163.06, 155.90, 153.93, 153.44, 147.82, 135.94, 131.34, 130.57, 129.35, 128.69, 128.34, 126.81, 125.87, 125.66, 123.88, 122.58, 119.86, 119.68, 119.04, 110.62, 110.45, 108.82; HRMS Calcd for C22H16N2O4 :372.1110, found 372.1095; Anal. (C22H16N2O4 0.4 H2O) C, H, N.

Sources & evidence

ORD record
ord-daaf56fbd8174269a850fcbfb24aacbc
Source dataset
uspto-grants-1997_03
Patent number
US05610192

Reaction notes

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