Isopropanol → HCID 86757068, compound

HRID 1069441Notes

Reaction equation

HRID 1069441 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=CC=C[CH:2]=1.[OH:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:23](=[O:33])[C:22]=1[N+:34]([O-:36])=[O:35].C(O)(C)C.CCOC(/N=N/C(OCC)=O)=O>C1C=CC=CC=1>[CH3:27][C:25]1[N:24]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:23](=[O:33])[C:22]([N+:34]([O-:36])=[O:35])=[C:21]([O:20][CH:1]([CH3:6])[CH3:2])[CH:26]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 54696200HCID 54696200, compound

Product 1

HCID 86757068HCID 86757068, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 11.38 g (43.4 mmol) of triphenylphosphine in 80 ml of benzene is cooled to 0° C. and 10 g (41.3 mmol) of methyl 4-hydroxy-6-methyl-3-nitro-2-oxo-1,2-dihydropyridine-1-acetate and 3.30 ml (43.37 mmol) of isopropanol are added. 6.83 ml (43.4 mmol) of diethylazodicarboxylate are then added dropwise and the mixture is left stirred for 48 hours. The reaction medium is washed successively with 50 ml of a saturated sodium hydrogen carbonate solution, 50 ml of water and 50 ml of a saturated sodium chloride solution. The medium is dried over magnesium sulphate and evaporated to dryness. The residue is purified by chromatography on a silica gel column, eluting with a dichloromethane:methanol (98:2) mixture.

Workup

  1. waitthe mixture is left
  2. washThe reaction medium is washed successively with 50 ml of a saturated sodium hydrogen carbonate solution, 50 ml of water and 50 ml of a saturated sodium chloride solution
  3. dry with materialThe medium is dried over magnesium sulphate
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography on a silica gel column
  6. washeluting with a dichloromethane:methanol (98:2) mixture

Sources & evidence

ORD record
ord-2d9f1884e4694dd1a5262084dbbb2dfc
Source dataset
uspto-grants-2001_06
Patent number
US06252082B1

Reaction notes

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