3-Nitrobenzaldehyde → HCID 57341997, compound

HRID 2279209Notes

Reaction equation

HRID 2279209 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-554a48d6611f4b059e15de267f786b20
Source dataset
uspto-grants-2015_09
Patent number
US09133214B2

Reaction notes

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