Water → HCID 53927100, compound

HRID 2038443Notes

Reaction equation

HRID 2038443 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:11][OH:12])[C:3](=[O:13])[O:2]1.[C:14](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.O>C1(C)C=CC=CC=1>[CH3:14][O:12][N:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1][O:2][C:3]1=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 73443586HCID 73443586, compound

Product 1

HCID 53927100HCID 53927100, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of isochroman-3,4-dione 4-oxime (90.4 HPLC-area %, 145.8 g, 0.74 mol) and potassium carbonate (153.4 g, 1.11 mol) in toluene (1000 mL) was stirred at ambient temperature for 1 h before dimethylsulfate (141.4 g, 1.11 mol) was added dropwise at 26° C. over a period of 2.5 h. The resulting mixture was stirred for 24 h at ambient temperature. After completion of the reaction, dist. water (1000 mL) was added to the mixture under stirring. The organic layer was separated, washed with dist. water (500 mL) and dried in vacuo at 30-50 mbar and max. 50° C. Isochroman-3,4-dione 4-(O-methyl-oxime) was obtained as a light orange solid (160.1 g, 88.7 HPLC-area %, quant. yield, diastereomeric ratio=58:42).

Workup

  1. additionwas added dropwise at 26° C. over a period of 2.5 h
  2. customAfter completion of the reaction, dist
  3. stirringunder stirring
  4. customThe organic layer was separated
  5. washwashed with dist
  6. dry with materialwater (500 mL) and dried in vacuo at 30-50 mbar and max
  7. custom50° C

Sources & evidence

ORD record
ord-d6ffca5b31cf45ee80abc391c719d997
Source dataset
uspto-grants-2013_11
Patent number
US08575366B2

Reaction notes

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