3-Nitrophenylboronic Acid → HCID 54174373, compound

HRID 342923Notes

Reaction equation

HRID 342923 reaction equation
[C:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:5][C:6]([OH:8])=O)#[N:2].[CH3:22][NH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[N+](C1C=C(B(O)O)C=CC=1)([O-])=O>C1(C)C=CC=CC=1>[C:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:5][C:6]([N:23]([CH3:22])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:8])#[N:2]

Participants

5

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 11503N-MethylbenzeneethanamineHCID 11011749HCID 11011749, compound

Product 1

HCID 54174373HCID 54174373, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.0 g of 4-cyano-4-(3,4-dimethoxy-phenyl)-5-methyl hexanoic acid (0.0172 mol) and 2.32 g, 2.50 ml of N-methylphenethylamine (0.0172 mol) in the presence of 30 mg of 3-nitrophenylboronic acid (~1 mol %) were set to reflux in 80 mls of toluene. The formed water was removed by use of Dean and Stark apparatus. After overnight heating GC/MS analysis indicated complete conversion of the acid (RT=25.07 mins) to the amide (RT=38.33 mins, m/z 408). After allowing to cool, the toluene solution was washed with 100 ml of 1.0N NaOH solution. The basic aqueous layer was re-extracted with 100 ml of toluene. The organic layers were combined and washed with 100 ml of water. The organic layers were dried over MgSO4, filtered and evaporated to dryness giving the amide in essentially quantitative yield as a yellow/green coloured oil. IR (liq film) ν (C=0)=1649.9 cm-1.

Workup

  1. customThe formed water was removed by use of Dean and Stark apparatus
  2. temperatureAfter overnight heating GC/MS analysis
  3. temperatureto cool
  4. washthe toluene solution was washed with 100 ml of 1.0N NaOH solution
  5. extractionThe basic aqueous layer was re-extracted with 100 ml of toluene
  6. washwashed with 100 ml of water
  7. dry with materialThe organic layers were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-ff3db26932d04d1b85f21e42fe5ab5bd
Source dataset
uspto-grants-1999_01
Patent number
US05859279

Reaction notes

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