3-Hydroxy-2-naphthoic acid hydrazide → HCID 136381078, compound

HRID 976061Notes

Reaction equation

HRID 976061 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][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][C:6]([OH:12])=[CH:7][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 519753HCID 519753, compound

Product 1

HCID 136381078HCID 136381078, compound

Procedure

Following the general procedure of Example 1, condensation of 2, 7-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded yellow crystals (83%) [recrystallized from DMSO/H2O (8:2, v/v)]: mp225° C. (dec); 1H NMR d 12.75 (s, 1 H), 12.24 (s, 1 H), 11.27 (s, 1 H), 9.93 (s, 1 H), 9.40 (s, 1H), 8.50 (s, 1 H), 7.95 (d, 1 H, J=8.1 Hz), 7.80 (d, 2 H, J=8.7 Hz), 7.73 (d, 1 H, J=8.7 Hz), 7.54 (t, 1 H, J=7.5 Hz), 7.39 (t, 1 H, J=7.5 Hz), 7.37 (s, 1 H), 6.98 (d, 2 H, J=8.7 Hz); HRMS Calcd for C22H16N2O4 :372.1110, found 372.1099; Anal. (C22H16N2O4 1.4 DMSO) C, H, N.

Workup

  1. customrecrystallized from DMSO/H2O (8:2

Sources & evidence

ORD record
ord-2ac4037a3e134186bbceba22869de581
Source dataset
uspto-grants-1997_03
Patent number
US05610192

Reaction notes

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