HCID 14256049, compound → HCID 15696376, compound

HRID 1647293Notes

Reaction equation

HRID 1647293 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N+:7]([C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=2)=[CH:12][CH:11]=1)([O-])=O>C1COCC1>[NH2:7][C:10]1[CH:11]=[CH:12][C:13](/[CH:16]=[CH:17]/[C:18]2[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14256049HCID 14256049, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15696376HCID 15696376, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (76 mg, 2 mmol) was added to a solution of nitro stilbene 6l (270 mg, 0.87 mmol) in THF (25 mL), and the mixture was stirred at room temperature for 12 h. Solvent was evaporated at reduced pressure, and the residue was decomposed by careful addition of ice water (20 mL) containing 2 mL of glacial acetic acid. The red solid formed was filtered and crystallized from CH2Cl2 -ether to give 6z (200 mg, 82%); mp 251°-3° C.; IR (KBr) 3440, 3400, 3000, 2920, 2820, 1600, 1580, 1510, 1340, 1240, 1130, 990, 950, 830 cm-1 ; 1H NMR (DMSO-d6, 300 MHz) δ7.87 (d, J=8.3 Hz, 2H), 7.59 (d, J=8.3 Hz, 2H), 7.08 (d, J-16.0 Hz, 1H), 7.01 (d, J= 16.0 Hz, 1H), 6.71 (s, 2H), 3.87 (s, 6H), 3 82 (s, 3H); CIMS (isobutane) m/e 286 (MH+, 100). Anal. (C17H19NO3) C, H.

Workup

  1. customSolvent was evaporated at reduced pressure
  2. additionthe residue was decomposed by careful addition of ice water (20 mL)
  3. additioncontaining 2 mL of glacial acetic acid
  4. customThe red solid formed
  5. filtrationwas filtered
  6. customcrystallized from CH2Cl2 -ether

Sources & evidence

ORD record
ord-e69dbb7ea56f40dba6c25edc01a6d710
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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