2-Hydroxy-1-naphthaldehyde → HCID 598517, compound

HRID 976058Notes

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.[NH2:14][NH:15][C:16]([NH:18][NH2:19])=[O: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:14][NH:15][C:16](=[O:17])[NH:18][N:19]=[CH:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[OH:1]

Participants

Reactant 2

HCID 128192-Hydroxy-1-naphthaldehyde

HCID 73948Carbohydrazide

Product 1

HCID 598517HCID 598517, compoundYield 97%

Procedure

Following the general procedure of Example 1, condensation of 2-hydroxy-1-naphthaldehyde and carbohydrazide gave a white solid (97%): mp>285° C. (dec); 1H NMR d 11.90 (br s, 2 H); 11.05 (s, 2 H), 9.23 (s, 2 H), 8.33 (d, 2 H, J=8.4 Hz), 7.88 (d, 2 H, J=9.0 Hz), 7.87 (d, 2 H, J=7.8 Hz), 7.59 (t, 2 H, J=7.6 Hz), 7.38 (t, 2 H, J=7.5 Hz), 7.22 (d, 2 H, J=9.0 Hz); 13C NMR d 156.71, 151.56, 143.24, 131.88, 131.50, 128.72, 127.87, 127.56, 123.35, 121.58, 118.61, 109.40; MS (CI) m/e 399.0 (M +H)+; Anal. (C23H18N4O3 0.3 H2O) C, H, N.

Sources & evidence

ORD record: ord-471787885e3d49e4a70620cbbf65ab94
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610192

Reaction notes

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