Hydrochloric Acid → HCID 86601368, compound

HRID 1182070Notes

Reaction equation

HRID 1182070 reaction equation
[CH2:1]([O:4][NH:5][CH:6]1[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][C:8]2[O:19][N:20]=[CH:21][C:7]1=2)[CH:2]=[CH2:3].Cl.[OH-].[NH4+]>C(OCC)(=O)C>[CH2:1]([O:4][NH:5][CH:6]1[CH2:11][NH:10][CH2:9][C:8]2[O:19][N:20]=[CH:21][C:7]1=2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86601369HCID 86601369, compound

Product 1

HCID 86601368HCID 86601368, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

1.24 g of the compound obtained in Stage C (4.21 mmoles) and 8.7 cm3 of ethyl acetate are placed in a 50 cm3 three-necked flask equipped with a magnetic stirrer and a temperature detector. The solution is cooled down to 0° C. then 8.7 cm3 of a saturated solution of gaseous HCl in ethyl acetate is added dropwise. Agitation is maintained for 5 minutes at 0° C. then the temperature of the solution is taken to 20° C. After agitating for two hours at 20° C., the solvent is evaporated off under reduced pressure in order to obtain a white powder to which an ethyl acetate/water mixture is added and a 20% solution of ammonium hydroxide is added. After dissolution and agitation for 10 minutes, decanting is carried out, followed by extracting again with 3× ethyl acetate. The organic phase is dried over MgSO4, filtered and rinsed with ethyl acetate. Finally, the solvent is evaporated off under reduced pressure in order to obtain 0.740 g of 4,5,6,7-tetrahydro-4-[(2-propenyloxy)amino]-isoxazolo[5,4-c]pyridine, of molecular formula C9H13N3O2 is obtained (M=195.22 g).

Workup

  1. customequipped with a magnetic stirrer
  2. temperatureAgitation is maintained for 5 minutes at 0° C.
  3. customis taken to 20° C
  4. customthe solvent is evaporated off under reduced pressure in order
  5. customto obtain a white powder to which an ethyl acetate/water mixture
  6. additionis added
  7. dissolutionAfter dissolution and agitation for 10 minutes
  8. customdecanting
  9. extractionby extracting again with 3× ethyl acetate
  10. dry with materialThe organic phase is dried over MgSO4
  11. filtrationfiltered
  12. washrinsed with ethyl acetate
  13. customFinally, the solvent is evaporated off under reduced pressure in order

Sources & evidence

ORD record
ord-9225719b51394504aa2cc5c2ce31fb7e
Source dataset
uspto-grants-2007_10
Patent number
US07288549B2

Reaction notes

Loading…