Ammonium Hydroxide → 3-Pyridinecarboxaldehyde, 2-amino-

HRID 897132Notes

Reaction equation

HRID 897132 reaction equation
Br[CH:2](Br)[C:3]1[C:4]([N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:5][CH:6]=[CH:7][CH:8]=1.[NH4+].[OH-:22]>C(O)C>[NH2:9][C:4]1[C:3]([CH:2]=[O:22])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 139254922-[3-(Dibromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 7376333-Pyridinecarboxaldehyde, 2-amino-Yield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

The compound was prepared according to the procedure as described by A. E. Moormann et al, Synthetic Communications, 17(14), 1695-1699 (1987) To a solution of 2-[3-(dibromomethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dione (20 g, 50 mmol) in ethanol (250 ml) was added conc. NH4OH (25 ml) at 4° C. The reaction mixture was stirred 10 minutes at 4° C. then stirred at room temperature for one hour. Reaction mixture was concentrated under reduced pressure. To the concentrated residue was added con. HCl (150 ml) and mixture was refluxed for 3 hours. The reaction mixture was cooled to room temperature and concentrated. To the concentrated residue was added water (25 ml) then added saturated K2CO3 to neutralize the solution. The solution was extracted with methylenechloride (3×150 ml). Combined organic solution was washed with water (3×150 ml), brine (1×200 ml), dried over Na2SO4, concentrated. The concentrated residue was suspended in ether, filtered and washed with ether to give 4.3 g (70%) yellow solid. NMR (DMSO) δ 6.69-6.73 (m, 1H), 7.51 (bs, 2H), 7.95-7.98(m, 1H), 8.20-8.22 (m, 1H), 9.82 (s, 1H).

Workup

  1. customThe compound was prepared
  2. stirringthen stirred at room temperature for one hour
  3. customReaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. additionTo the concentrated residue was added con
  6. temperatureHCl (150 ml) and mixture was refluxed for 3 hours
  7. temperatureThe reaction mixture was cooled to room temperature
  8. concentrationconcentrated
  9. additionTo the concentrated residue was added water (25 ml)
  10. extractionThe solution was extracted with methylenechloride (3×150 ml)
  11. washCombined organic solution was washed with water (3×150 ml), brine (1×200 ml)
  12. dry with materialdried over Na2SO4
  13. concentrationconcentrated
  14. filtrationfiltered
  15. washwashed with ether

Sources & evidence

ORD record
ord-f29af0150fd44d3e88a7ba3ec79db666
Source dataset
uspto-grants-2005_07
Patent number
US06921767B2

Reaction notes

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