O-Phenylenediamine → HCID 22675416, compound

HRID 1005962Notes

Reaction equation

HRID 1005962 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]C)=O.[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].C([O-])(O)=O.[Na+]>Cl>[OH:10][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1[NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:19]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 516892Sodium BicarbonateHCID 10986540HCID 10986540, compound

Product 1

HCID 22675416HCID 22675416, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1.6 g of methyl 7-hydroxyheptanoate and 1.08 g of o-phenylenediamine were refluxed for 7 hours in 15 ml of 2:1 hydrochloric acid aqueous solution. The reaction mixture was cooled to room temperature, then adjusted to pH 8 with addition of aqueous NaHCO3 and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to obtain 0.9 g of the title compound (yield: 41%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-25437be7cbef4d5ca7086579b01663ee
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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