Hydrochloric Acid → HCID 10064943, compound

HRID 1742100Notes

Reaction equation

HRID 1742100 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][N:9]=[C:10](OCC)[CH2:11][CH2:12][CH2:13][CH3:14])=O.[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].Cl>C(O)C>[CH2:11]([C:10]1[N:26]([CH2:25][C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:28][CH:27]=2)[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:8][N:9]=1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 291474-NitrobenzylamineHCID 54254679HCID 54254679, compound

Product 1

HCID 10064943HCID 10064943, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 678 mg (2.85 mmole) of ethyl valerate 2-furoylhydrazone dissolved in 3 ml of ethanol was added a solution of 514 mg (2.16 mmole ) of 4-nitrobenzylamine (generated from the hydrochloride by partitioning between ether and saturated Na2CO3 solution) in 3 ml of ethanol. The resulting solution was heated at 45°-50° C. for two hours and then at 70° C. overnight. The solution was cooled and concentrated. Column chromatography of the residue on silica gel (gradient elution with 0.5-2.5% methanol in CH2Cl2) afforded some recovered starting material (ester hydrazone) followed by 432 mg (61%) of the product as a yellow oil which upon standing at 5° C. crystallized to a solid having mp 91°-92.5° C., homogeneous by TLC in 97:3 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 327 (M+1)+.

Workup

  1. customby partitioning between ether and saturated Na2CO3 solution) in 3 ml of ethanol
  2. temperatureThe resulting solution was heated at 45°-50° C. for two hours
  3. customat 70° C.
  4. customovernight
  5. temperatureThe solution was cooled
  6. concentrationconcentrated
  7. customColumn chromatography of the residue on silica gel (gradient elution with 0.5-2.5% methanol in CH2Cl2) afforded some recovered
  8. customupon standing at 5° C.
  9. customcrystallized to a solid

Sources & evidence

ORD record
ord-25e4d9c03fa043278f1014e04dffae59
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

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