3-Nitrobenzaldehyde → HCID 57341997, compound

HRID 1097284Notes

Reaction equation

HRID 1097284 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH3:12][NH:13][CH2:14][CH:15]=[CH2:16].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:14]([N:13]([CH3:12])[CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 69391N-MethylallylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57341997HCID 57341997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 3-nitrobenzaldehyde (1.5 g, 9.92 mmol) in CH2Cl2 (60 mL) was added N-methyl allyl amine (1.19 g, 12.40 mmol), the reaction mixture was stirred for 2 h. Na(OAc)3BH (4.2 g, 19.85 mmol) was then added portionwise over 5 mins. The resulting mixture was stirred at ambient temperature overnight and then quenched with saturated NH4Cl. The product was extracted with CH2Cl2 thrice and the combined organic extracts were washed brine, dried over Na2SO4 and concentrated under reduced pressure. The crude mixture was column purified (EtOAc/Hexane) to furnish 1.1 g of (xA). 1H NMR (400 MHz, CDCl3): δ 8.20 (m, 1H), 8.08-8.12 (m, 1H), 7.65-7.69 (m, 1H), 7.48 (t, 1H), 5.84-5.96 (m, 1H), 5.12-5.26 (m, 2H), 3.58 (s, 2H), 3.02-3.06 (m, 2H), 2.20 (s, 3H). MS (m/z): 207 [MH]+.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature overnight
  2. customquenched with saturated NH4Cl
  3. extractionThe product was extracted with CH2Cl2 thrice
  4. washthe combined organic extracts were washed brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified (EtOAc/Hexane)
  8. customto furnish 1.1 g of (xA)

Sources & evidence

ORD record
ord-5fcf6155697c42818a5ff60bb490c741
Source dataset
uspto-grants-2012_03
Patent number
US08143255B2

Reaction notes

Loading…