Salicylaldehyde → 3-Hydroxy-N-[(2-hydroxyphenyl)methylidene]naphthalene-2-carbohydrazonic acid

HRID 976064Notes

Reaction equation

HRID 976064 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]=O)[C:4]([OH:9])=[CH:3][CH:2]=1.[OH:10][C:11]1[C:12]([C:21]([NH:23][NH2:24])=[O:22])=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2>>[OH:9][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH:7]=[N:24][NH:23][C:21]([C:12]1[C:11]([OH:10])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)=[O:22]

Participants

3

Reactant 2

HCID 6998SalicylaldehydeHCID 726993-Hydroxy-2-naphthoic acid hydrazide

Product 1

HCID 3117343-Hydroxy-N-[(2-hydroxyphenyl)methylidene]naphthalene-2-carbohydrazonic acidYield 94%

Procedure

Following the general procedure of Example 1, condensation of salicylic aldehyde and 3-hydroxy-2-naphthoic hydrazide gave a pale yellow solid (94%): mp >285° C.; 1H NMR d 11.69 (br s, 1H), 10.97 (br s, 1 H), 10.79 (s, 1 H), 8.24 (s, 1 H), 8.02 (s, 1 H), 7.45 (d, 1 H, J=8.1 Hz), 7.31 (d, 1 H, J=8.1 Hz), 7.12 (dd, 1 H, J=7.8, 0.9 Hz), 7.05 (t, 1 H, J=7.5 Hz), 6.89 (s, 1 H), 6.86 (m, 2H), 6.51 (d, 1 H, J=8.1 Hz), 6.48 (t, 1H, J=7.5 Hz); 13C NMR d 163.62, 157.54, 154.08, 148.83, 135.94, 131.64, 130.37, 129.49, 128.70, 128.33, 126.79, 125.89, 123.86, 119.99, 119.44, 118.68, 116.48, 110.63; HRMS Calcd for C18H14N2O3 :306.1004, found 306.0977; Anal. (C18H14N2O3) C, H, N.

Sources & evidence

ORD record
ord-45d83b3f77a5489f92acab6a46408a07
Source dataset
uspto-grants-1997_03
Patent number
US05610192

Reaction notes

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