3-Hydroxy-2-naphthoic acid hydrazide → HCID 136381077, compound

HRID 976060Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[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]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[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

Reactant 2

HCID 726993-Hydroxy-2-naphthoic acid hydrazide

HCID 21953759HCID 21953759, compound

Product 1

HCID 136381077HCID 136381077, compoundYield 83%

Procedure

Following the general procedure of Example 1, condensation of 2, 4-dihydroxy-1-naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide yielded a yellow crystal (83%) [recrystallized from DMSO/H2O (8:2, v/v)]: mp>280° C. (dec); 1H NMR d 12.42 (br s, 1 H), 11.65 (s, 1 H), 10.96 (br s, 1 H), 10.59 (s, 1 H), 8.99 (s, 1H), 8.07 (s, 1H), 7.77 (d, 1 H, J=8.4 Hz), 7.67 (d, 1 H, J=8.4 Hz), 7.48 (d, 1 H, J=8.1 Hz), 7.32 (d, 1H, J=8.4 Hz), 7.13 (t, 1H, J=7.5 Hz), 7.06 (t, 1 H, J=7.5 Hz), 6.91 (s, 1 H), 6.90 (m, 2 H); 13C NMR d 162.92, 160.47. 157.70, 154.20, 148.22, 135.97, 132.99, 130.33, 128.72, 128.33 (2 C), 126.84, 125.92, 123.91, 122.94, 122.55, 120.80, 120.32, 119.66, 110.70, 101.38, 100.49; HRMS Calcd for C22H16N2O4 :372.1110, found 372.1095; Anal. (C22H16N2O4 2DMSO H2O) C, H, N.

Sources & evidence

ORD record: ord-f3b1c4bf0247451dbebc27292ef98ba6
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610192

Reaction notes

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