1-Naphthaldehyde → HCID 2164190, compound

HRID 976063Notes

Reaction equation

[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH:13][C:14]1[C:15]([C:24]([NH:26][NH2:27])=[O:25])=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2>>[C:1]1([CH:11]=[N:27][NH:26][C:24]([C:15]2[C:14]([OH:13])=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[O:25])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 61951-Naphthaldehyde

HCID 726993-Hydroxy-2-naphthoic acid hydrazide

Product 1

HCID 2164190HCID 2164190, compoundYield 76%

Procedure

Following the general procedure of Example 1, condensation of 1naphthaldehyde and 3-hydroxy-2-naphthoic hydrazide gave a pale yellow solid (76%): mp 214° C.; 1H NMR d 11.73 (br s, 1 H), 11.05 (br s, 1 H), 8.72 (s, 1 H), 8.52 (d, 1 H, J=8.4 Hz), 8.13 (s, 1 H), 7.60-6.80 (m, 11 H); 13C NMR d 164.00, 154.31, 148.56, 135.99, 133.57, 130.80, 130.40. 130.30, 129.48, 128.81, 128.78, 128.29, 128.12, 127.37, 126.85, 126.31. 125.89, 125.54, 124.39, 123.84, 120.13, 110.75; HRMS Calcd for C22H16N2O2 :340.1212, found 340.1208; Anal. (C22H16N2O2) C, H, N.

Sources & evidence

ORD record: ord-36607ec1d42940318737e612c15177be
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610192

Reaction notes

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