Ammonium Hydroxide → HCID 9909712, compound

HRID 1018516Notes

Reaction equation

HRID 1018516 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]([C:10]1[CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])[C:12]([C:18]([O:20][CH3:21])=[O:19])=[C:13]([CH3:17])[NH:14][C:15]=1[CH3:16])=[O:9].[NH4+].[OH-]>C(O)(=O)C>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[C:12]([C:18]([O:20][CH3:21])=[O:19])[C:13]([CH3:17])=[N:14][C:15]=1[CH3:16])=[O:9]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 65988Methyl (oxolan-2-yl)methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 9909712HCID 9909712, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 30 g (0.07 mol) of 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-(tetrahydrofuran-2-ylmethyl) ester in 72 ml of acetic acid, heated to reflux, 7.2 g (0.07 mol) of CrO3 were portionwise added. After the addition was complete, reflux was maintained for one additional hour. The reaction mixture was then slowly poured on ice-cooled aq NH4OH (150 ml). The mixture separated in two phases, and it was evacuated with CH2Cl2 (3×100 ml). The organic extract was dried with anh Na2SO4, and concentrated to dryness at reduced pressure. The resulting oil was crystallised in EtAcO-diethylether, yielding a white solid (mp 69-70° C., EtOH) with a yield of 79%.

Workup

  1. temperatureto reflux
  2. additionAfter the addition
  3. temperaturereflux
  4. temperaturewas maintained for one additional hour
  5. additionThe reaction mixture was then slowly poured on ice-
  6. customThe mixture separated in two phases, and it
  7. customwas evacuated with CH2Cl2 (3×100 ml)
  8. extractionThe organic extract
  9. dry with materialwas dried with anh Na2SO4
  10. concentrationconcentrated to dryness at reduced pressure
  11. customThe resulting oil was crystallised in EtAcO-diethylether
  12. customyielding a white solid (mp 69-70° C., EtOH) with a yield of 79%

Sources & evidence

ORD record
ord-a90682b1b4b4488e82d0026597ed1fe4
Source dataset
uspto-grants-2002_11
Patent number
US06482841B1

Reaction notes

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