Hydrochloric Acid → HCID 73991630, compound

HRID 2188346Notes

Reaction equation

HRID 2188346 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1)[CH3:2].C([O:19][N:20]=O)CC(C)C.Cl>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C:9](=[N:20][OH:19])[C:10]2=[O:13])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 150391526-Ethoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 73991630HCID 73991630, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
7.5 °C

Procedure

A solution of 6-ethoxy-1-indanone and isoamylnitrite (1.5 eq.) in ethyl acetate arecooled to approximately 0° C. and concentrated hydrochloric acid (1.1 acid equivalents) is added at a rate to keep the temperature below 40° C. After the addition is completed the slurry is stirred at 5-10° C. until analysis indicated that all of the starting material is consumed. The product is filtered and rinsed with cold ethyl acetate. The oxime product (5) can be easily purified by refluxing as a slurry in anhydrous ethanol, cooling filtering, and then washing the solid with more ethanol and then drying (m.p. 220° C. decomp.).

Workup

  1. customarecooled to approximately 0° C.
  2. customthe temperature below 40° C
  3. additionAfter the addition
  4. customis consumed
  5. filtrationThe product is filtered
  6. washrinsed with cold ethyl acetate
  7. customThe oxime product (5) can be easily purified
  8. temperatureby refluxing as a slurry in anhydrous ethanol
  9. temperaturecooling
  10. filtrationfiltering
  11. washwashing the solid with more ethanol
  12. customdrying (m.p. 220° C. decomp.)

Sources & evidence

ORD record
ord-1c27a6d95735431b820e44a6e93949a4
Source dataset
uspto-grants-2002_06
Patent number
US06410787B1

Reaction notes

Loading…