Borane;pyridine → HCID 68017766, compound

HRID 1498919Notes

Reaction equation

HRID 1498919 reaction equation
B.N1C=CC=CC=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[N:17][N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])=[CH:12][C:11]=1[CH3:29]>C(O)(=O)C>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])=[CH:12][C:11]=1[CH3:29]

Participants

4

Reactant 2

HCID 2723995Borane;pyridineHCID 77531930HCID 77531930, compound

Product 1

HCID 68017766HCID 68017766, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (40 ml) and pyridine-borane (4.3 ml) were added to 2-{[1-(4-methoxy-3-methylphenyl)-methylidene]amino}isoindole-1,3-dione (2.50 g) prepared in the Step 15-1-1, and the mixture was stirred under a room temperature for 0.5 hours. The mixture was concentrated under a reduced pressure, and under an ice cooling 10% hydrochloric acid (10 ml) was added to the resulting residue. Sodium hydroxide (1.1 g) was added thereto, and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated saline solution, and then dried over sodium sulfate and concentrated under a reduced pressure. To the resulting residue, ethanol (10 ml) was added, and the mixture was stirred at a room temperature. The precipitate was separated by filtration, washed with ethanol, and concentrated under a reduced pressure to give the title compound (1.71 g, 68%).

Workup

  1. customprepared in the Step 15-1-1
  2. concentrationThe mixture was concentrated under a reduced pressure
  3. additionunder an ice cooling 10% hydrochloric acid (10 ml) was added to the resulting residue
  4. additionSodium hydroxide (1.1 g) was added
  5. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. additionTo the resulting residue, ethanol (10 ml) was added
  10. stirringthe mixture was stirred at a room temperature
  11. customThe precipitate was separated by filtration
  12. washwashed with ethanol
  13. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-bd8065438682484ea7730319b279c96a
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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