2-Hydroxy-1-naphthaldehyde → HCID 598053, compound

HRID 976065Notes

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.[C:14]([NH:23][NH2:24])(=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17]>>[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:24][NH:23][C:14](=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17]

Participants

Reactant 2

HCID 128192-Hydroxy-1-naphthaldehyde

HCID 13637Salicylic acid, hydrazide

Product 1

HCID 598053HCID 598053, compoundYield 74%

Procedure

Following the general procedure of Example 1, condensation of 2-hydroxy-1-naphthaldehyde and salicylic hydrazide yielded a pale yellow solid (74%): mp 265° C.; 1H NMR d 12.32 (s, 1 H), 11.65 (br s, 1 H), 11.36 (br s, 1 H), 9.09 (s, 1 H), 7.84 (d, 1 H, J=7.5 Hz), 7.43 (m, 3 H), 7.13 (t, 1 H, J=6.0 Hz), 7.01 (t, 1 H, J=6.6 Hz), 6.83 (t, 1H, J=6.9 Hz), 6.77 (d, 1H, J=8.4 Hz), 6.57 (m, 2 H); 13C NMR d 163.72, 158.58, 157.88, 147.40, 133.75, 132.63, 131.42, 128.64, 128.49, 127.53, 127.44, 123.27, 120.65, 118.87, 118.61, 117.04, 115.35, 108.32; HRMS Calcd for C18H14N2O3 :306.1004, found 306.0985; Anal. (C18H14N2O3) C, H, N.

Sources & evidence

ORD record: ord-4d8a3254482541eba4b45a664d1c7366
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610192

Reaction notes

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