Hydrochloric Acid → HCID 69205088, compound

HRID 131054Notes

Reaction equation

HRID 131054 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[ClH:21]>CO>[ClH:21].[ClH:21].[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58596146HCID 58596146, compound

Product 1

HCID 69205088HCID 69205088, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.3 g of nitro derivative (14) prepared above and about 100 ml of methanol were introduced into a 200 ml autoclave (hydrogenator) equipped with a magnetic stirrer. The solution obtained was degassed with nitrogen. 0.4 g of palladium-on-charcoal (5% humidity, containing 50% water) was added thereto. The reaction mixture was stirred, while flushing once with hydrogen, and hydrogen was then introduced to a pressure of about 5 bar. After reaction for 4 hours, the reactor was flushed with nitrogen. The reaction mixture was filtered quickly through Celite under a gentle pressure of nitrogen. The filtrate was recovered into a precooled solution of methanol containing about 3 equivalents of hydrogen chloride gas. The filter cake was rinsed several times with methanol under a stream of nitrogen. The solution thus obtained was concentrated and then treated with ether. The product obtained, in the form of a pale pink paste, was stirred and then rinsed several times with acetonitrile and with ether under nitrogen. 2.1 g of expected product (15) were isolated in the form of a slightly pink-white powder.

Workup

  1. additionwere introduced into a 200 ml autoclave (hydrogenator)
  2. customequipped with a magnetic stirrer
  3. customThe solution obtained
  4. customwas degassed with nitrogen
  5. addition0.4 g of palladium-on-charcoal (5% humidity, containing 50% water) was added
  6. customwhile flushing once with hydrogen, and hydrogen
  7. additionwas then introduced to a pressure of about 5 bar
  8. customAfter reaction for 4 hours
  9. customthe reactor was flushed with nitrogen
  10. filtrationThe reaction mixture was filtered quickly through Celite under a gentle pressure of nitrogen
  11. washThe filter cake was rinsed several times with methanol under a stream of nitrogen
  12. customThe solution thus obtained
  13. concentrationwas concentrated
  14. additiontreated with ether
  15. customThe product obtained, in the form of a pale pink paste
  16. stirringwas stirred
  17. washrinsed several times with acetonitrile

Sources & evidence

ORD record
ord-a0d5a58d5ada4edda1e5dc96b0bc23b4
Source dataset
uspto-grants-2008_06
Patent number
US07384432B2

Reaction notes

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