Water → Benmoxin

HRID 592110Notes

Reaction equation

HRID 592110 reaction equation
[C:1]1(/[C:7](=[N:9]/[NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O)(=O)=O.O.COC(OC)(C)C.[H][H]>CC(C)=O>[C:1]1([CH:7]([NH:9][NH:10][C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 64952,2-DimethoxypropaneHCID 9574244N'-(1-Phenylethylidene)benzohydrazide2×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 71671Benmoxin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 120 mL high-pressure autoclave were charged (E)-N′-(1-phenylethylidene)benzohydrazide (119 mg) [mw. 238.28, 0.5 mmol], [Rh(cod) (S,S)-ptbp-skewphos)]OTf (5.1 mg) [mw. 1025.08, 5.0 μmol, s/c 100], and methanesulfonic acid (0.5 mg) [mw. 96.11, 5.0 μmol, 0.01 eq.]. The system was argon-substituted 7 times. 10 mL Schlenk flask was substituted with argon, and pure water (9 mg) [mw. 18.02, 0.5 mmol, 1.0 eq.], 2,2-dimethoxypropane (0.18 mL) [mw. 104.15, d=0.85, 1.5 mmol, 3.0 eq.] and dehydrated acetone for organic synthesis (5 mL) were added. The solution was fed into an autoclave by argon pressure supply. The system was substituted with hydrogen gas, and the mixture was stirred with hydrogen gas pressurization at 1.0 MPa for 2 hr. The system was depressurized, and analyzed by high performance liquid chromatography to find that the starting material, (E)-N′-(1-phenylethylidene)benzohydrazide, remained by 38%, and the resultant product, N′-(1-phenylethyl)benzohydrazide was produced by 59%, and the decomposed product, acetophenone, was produced by 1%.

Workup

  1. customfor organic synthesis (5 mL)
  2. additionwere added

Sources & evidence

ORD record
ord-d52766af16c34801b26bb805651bef1e
Source dataset
uspto-grants-2016_01
Patent number
US09238667B2

Reaction notes

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