Hydrazine → Ethyl 4-hydrazino-2-(3'-nitrophenyl)pyrimidine-5-carboxylate

HRID 1584862Notes

Reaction equation

HRID 1584862 reaction equation
O[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[N:3]=1.[Cl-].ClC=[N+](C)C.ClC1C(C(OCC)=O)=CN=C(C2C=CC=C([N+]([O-])=O)C=2)N=1.[NH2:49][NH2:50]>CCOCC.CCCCCC>[NH:49]([C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[N:3]=1)[NH2:50]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 21220671Ethyl 4-chloro-2-(3'-nitrophenyl)pyrimidine-5-carboxylate2×HCID 178469743HCID 178469743, compound

Product 1

HCID 21220603Ethyl 4-hydrazino-2-(3'-nitrophenyl)pyrimidine-5-carboxylateYield 33%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared by (a) reaction of diethyl ethoxymethylenemalonate (5 g, 24 mmol) with 3-nitrobenzamidine (5 g, 25 mmol) to afford 86% of ethyl 4-hydroxy-2-(3'-nitrophenyl)pyrimidine-5-carboxylate in analogy to Example 15, (b) reaction of ethyl 4-hydroxy-2-(3'-nitrophenyl)pyrimidine-5-carboxylate (6 g, 21 mmol) with (chloromethylene)dimethylammonium chloride (4 g, 31 mmol) concentration of reaction mixture, followed by hexane and ether wash afford 45% of ethyl 4-chloro-2-(3'-nitrophenyl)pyrimidine-5-carboxylate, (c) reaction of ethyl 4-chloro-2-(3'-nitrophenyl)pyrimidine-5-carboxylate (1.9 g, 6 mmol) with hydrazine (0.6 g, 18 mmol) to afford 33% of ethyl 4-hydrazino-2-(3'-nitrophenyl)pyrimidine-5-carboxylate in analogy to Example 18, (d) reaction of ethyl 4-hydrazino-2-(3'-nitrophenyl)pyrimidine-5-carboxylate (1.8 g, 6 mmol) with citraconic anhydride in analogy to Example 21, to afford 80% (0.5 g) of the title compound; m.p. 118-120° C.

Workup

  1. washwash
  2. customafford

Sources & evidence

ORD record
ord-33a042d8ad1d4f9e8ec3f2397e8d2b96
Source dataset
uspto-grants-1999_08
Patent number
US05935966

Reaction notes

Loading…