Hydrochloric Acid → HCID 73443586, compound

HRID 2038442Notes

Reaction equation

HRID 2038442 reaction equation
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1.C[O-:13].[Na+].[N:15](OCC(C)C)=[O:16].Cl>CO>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:15][OH:16])[C:3](=[O:13])[O:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10958Isobutyl nitriteHCID 784293,4-DihydroisocoumarinHCID 10942334Sodium Methoxide

Product 1

HCID 73443586HCID 73443586, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

To a suspension of isochromanone (99% pure, 149.7 g, 1.00 mol) in methanol (280 mL) was added dropwise over a period of 90 min at 14-16° C. sodium methanolate (30% in methanol, 270.0 g, 1.50 mol) and the resulting mixture was stirred for 90 min at 15° C. To this mixture was added dropwise over a period of 6.5 h at 9-13° C. iso-butyl nitrite (94% pure, 137.1 g, 1.25 mol) and the mixture was stirred at 8° C. overnight. The conversion was monitored by HPLC. After completion of the reaction, 4 M hydrochloric acid was added to adjust a pH<1 before the resulting suspension was stirred for overnight at 4° C. The crude product was collected by filtration, washed with cold dist. water (2×500 mL) and dried in vacuo at max. 45° C. Isochroman-3,4-dione-4-oxime was obtained as a colorless solid (145.9 g, 90.4 HPLC-area %, 74% yield).

Workup

  1. stirringthe mixture was stirred at 8° C. overnight
  2. additionwas added
  3. stirringwas stirred for overnight at 4° C
  4. filtrationThe crude product was collected by filtration
  5. washwashed with cold dist
  6. dry with materialwater (2×500 mL) and dried in vacuo at max
  7. custom45° C

Sources & evidence

ORD record
ord-0613f6d618d348169f2fdab2e64beb37
Source dataset
uspto-grants-2013_11
Patent number
US08575366B2

Reaction notes

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