Hydrochloric Acid → 2-Hydroxy-1-naphthaldehyde-o-aminobenzoyl hydrazone

HRID 1156089Notes

Reaction equation

HRID 1156089 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].COC(C1C(N)=CC=CC=1)=O.NN.C1C2C(=CC=CC=2)C=CC=1O.C=O.C1N2CN3CN(C2)CN1C3.Cl.[OH:49][C:50]1[CH:59]=[CH:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:51]=1[CH:60]=O>C(O)(=O)C>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][N:7]=[CH:60][C:51]1[C:52]2[C:57](=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:58]=[CH:59][C:50]=1[OH:49])=[O:5]

Participants

10

Reactant 8

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 4101HexamethylenetetramineHCID 8635Methyl AnthranilateHCID 86632-NaphtholHCID 9321HydrazineHCID 128192-Hydroxy-1-naphthaldehydeHCID 94728Benzoic acid, 2-amino-, hydrazide2×

Product 1

HCID 30849512-Hydroxy-1-naphthaldehyde-o-aminobenzoyl hydrazoneYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In reaction (1), o-aminobenzhydrazide in 70% yield is prepared by reacting the methyl ester of o-amino benzoic acid (methyl anthranilate) with 64% aqueous hydrazine. Equation (2) illustrates the preparation of 2-hydroxy-1-naphthaladehyde from beta-naphthol, paraformaldehyde, hexamethylene tetramine, acetic acid and hydrochloric acid. o-Aminobenzhydrazide and 2-hydroxy-1-naphthaldehyde are reacted, in Equation (3), to produce the preferred hydrazone, 2-hydroxy-1-naphthaldehyde-o-aminobenzoyl hydrazone in 80-90% yield.

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-c6aac1509044478383a173aad1c1e336
Source dataset
uspto-grants-1982_06
Patent number
US04334015

Reaction notes

Loading…