Pyridine → Diethyl 1,4-dihydro-2-methyl-4-(3-nitrophenyl)-6-(4-nitrophenyl)-3,5-pyridinedicarboxylate

HRID 1789023Notes

Reaction equation

HRID 1789023 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1.O[C:21]1([C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)[CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=2)[C:24]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:23]([CH3:46])[NH:22]1>C(Cl)Cl>[CH3:46][C:23]1[NH:22][C:21]([C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=2)[C:24]=1[C:41]([O:43][CH2:44][CH3:45])=[O:42]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 20189315Diethyl 1,2,3,4-tetrahydro-2-hydroxy-6-methyl-4-(3-nitrophenyl)-2-(4-nitrophenyl)-3,5-pyridinedicarboxylate

Product 1

HCID 20189318Diethyl 1,4-dihydro-2-methyl-4-(3-nitrophenyl)-6-(4-nitrophenyl)-3,5-pyridinedicarboxylateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (0.65 ml, 4.63 mmoles) was added with stirring to pyridine (0.75 ml, 9.26 mmoles) and diethyl 1,2,3,4-tetrahydro-2-hydroxy-6-methyl-4-(3-nitrophenyl)-2-(4-nitrophenyl)-3,5-pyridinedicarboxylate (2.31 g, 4.63 mmoles) in methylene chloride (60 ml). After stirring for 2.5 hours, the solution was washed with water, dilute hydrochloric acid (x3), water, saturated sodium bicarbonate solution, water and dried (Na2SO4). The solvent was removed in vacuo and the residue recrystallised from ethanol to give the title compound (1.77 g) as a yellow solid, mp 176°-7°.

Workup

  1. washthe solution was washed with water, dilute hydrochloric acid (x3), water, saturated sodium bicarbonate solution, water
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was removed in vacuo
  4. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-c568eb9ea3b2481a8e9057cadfb1c622
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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