Water → HCID 178507546, compound

HRID 2350837Notes

Reaction equation

HRID 2350837 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[CH:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[N+:11]=2[O-:27])=[CH:6][CH:5]=1)([O-])=O.[S-2].[Na+].[Na+].O>C(O)C>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH:17]=[CH:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([CH:9]=[CH:8][C:7]3[CH:28]=[CH:29][C:4]([NH2:1])=[CH:5][CH:6]=3)[N+:11]=2[O-:27])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14804Sodium SulfideHCID 3565458HCID 3565458, compound

Product 1

HCID 178507546HCID 178507546, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

More specifically, the synthesizing procedure is as follows. 2,6-dimethylpyridine or a substituted product thereof, is reacted with p-nitrobenzenealdehyde or a substituted product according to a method described, for example, in Journal of Organic Chemistry, vol. 15, P. 1184 (1950) to synthesize 2,6-di(p-nitrostyryl)pyridine (K). 30 g of this nitro compound is reacted wtih 27 g of m-chloroperbenzoic acid in three liter of dichloromethane to obtain 24 g of 2,6-di(p-nitrostyryl)pyridine-N-oxide. 24 g of this pyridine-N-oxide is reacted with 90 g of sodium sulfide in a solution mixed four liter of water with four liter of ethanol to reduce nitro group selectively and form 18 g of 2,6-di(p-aminostyryl)pyridine-N-oxide (M). The N-oxide amino compound is converted into a diazo compound according to a conventional method, and thereby tetrazonium salt is isolated as 15 g of hydroborofluoric salt (N). 5.0 g of the tetrazonium salt (N) and 5.0 g of 2-hydroxy-3-phenylcarbamoylnaphthalene (O) were dissolved in one liter of DMF, to which aqueous sodium acetate solution (7 g/100 ml) was added to perform coupling reaction. After two hours of stirring, the resultant crystals were separated by filtration, and the crystals were rinsed three times respectively with five liter water, three times respectively with five liter THF, then dried, to obtain 4.0 g of the final product, azo compound (P - 1).

Sources & evidence

ORD record
ord-9de733d0aa844746a233cb060930c6dc
Source dataset
uspto-grants-1989_10
Patent number
US04871633

Reaction notes

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