O-Phenylenediamine → HCID 10729798, compound

HRID 2293106Notes

Reaction equation

HRID 2293106 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]12([CH:19]=O)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.[BH4-].[Na+]>CO.C(OCC)(=O)C>[C:9]12([CH2:19][NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[NH2:8])[CH2:10][CH:11]3[CH2:17][CH:15]([CH2:14][CH:13]([CH2:12]3)[CH2:18]1)[CH2:16]2

Participants

6

Reactant 3

HCID 7243O-PhenylenediamineHCID 4311764Sodium borohydrideHCID 110410501-Adamantanecarboxaldehyde

Product 1

HCID 10729798HCID 10729798, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2-Phenylenediamine (5 g) was added to a solution of 1-adamantanecarboxaldehyde (7.6 g) in methanol (100 ml). The solution was stirred at 23° for 2 h, then sodium borohydride (3.5 g) was added portionwise. The resulting mixture was stirred at 230 for 2 h, then diluted with ethyl acetate (400 ml) and filtered. The organic layer was washed with brine (300 ml), dried and concentrated in vacuo to a residue, which was taken up in ethyl ether and the inorganic salts still present were removed by filtration. The filtrate was concentrated in vacuo and purified by flash chromatography to give the title compound as a beige solid (1.2 g). M.p.86°-7° T.l.c. CH-EA (7:3), Rf 0.6.

Workup

  1. stirringThe resulting mixture was stirred at 230 for 2 h
  2. filtrationfiltered
  3. washThe organic layer was washed with brine (300 ml)
  4. customdried
  5. concentrationconcentrated in vacuo to a residue, which
  6. customthe inorganic salts still present were removed by filtration
  7. concentrationThe filtrate was concentrated in vacuo
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-05c2a13196154807bf3d622b099ebca8
Source dataset
uspto-grants-1997_11
Patent number
US05686449

Reaction notes

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