Hydrazine hydrate (1:1) → 1,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(2,3-dichlorophenyl)-5-(2-aminoethoxy)carbonyl-pyridine

HRID 845265Notes

Reaction equation

HRID 845265 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:36])=[C:5]([C:20]([O:22][CH2:23][CH2:24][N:25]2C(=O)C3=CC=CC=C3C2=O)=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9].O.NN>C(OC)(C)(C)C>[CH3:1][C:2]1[NH:3][C:4]([CH3:36])=[C:5]([C:20]([O:22][CH2:23][CH2:24][NH2:25])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 140116751,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(2,3-dichlorophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridine

Product 1

HCID 140116791,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(2,3-dichlorophenyl)-5-(2-aminoethoxy)carbonyl-pyridineYield 51%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Prepared by a method analogous to that of Example 1(b) from 10.0 g (19 mmol) of 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(2,3-dichlorophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridine and 2.84 ml (57 mmol) of hydrazine hydrate. 3.85 g (51%) of pale yellow crystals melting at 166°-167° C. obtained from tert.-butylmethyl ether.

Sources & evidence

ORD record
ord-43ac57270ae34c909a973a788eda284c
Source dataset
uspto-grants-1988_07
Patent number
US04757080

Reaction notes

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