3-Nitrobenzaldehyde → HCID 4618037, compound

HRID 1157584Notes

Reaction equation

HRID 1157584 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][N:13]([CH3:17])[CH2:14][CH2:15][NH2:16].C([BH3-])#N.[Na+]>CC(O)=O.C(Cl)Cl>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][NH:16][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 66053N,N-DimethylethylenediamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 4618037HCID 4618037, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 3-nitrobenzaldehyde (127 mg, 0.84 mmol), N,N-dimethylethylenediamine (184 μL, 1.7 mmol), and HOAc (5 drops) in DCM (10 mL) was stirred at rt for 6 h and then heated to 40° C. for 1 hour. The reaction was cooled to 0° C., and sodium cyanoborohydride (360 mg, 1.7 mmol) was added in one portion. The reaction was stirred overnight at rt. After 16 h, the reaction mixture was washed with 4 N NaOH, dried over Na2SO4, and concentrated. The crude product was used in the next reaction without further purification. ES-LC/MS m/z=224 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. waitAfter 16 h
  3. washthe reaction mixture was washed with 4 N NaOH
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was used in the next reaction without further purification

Sources & evidence

ORD record
ord-6792ccfec04943b7ab6afb7c40890a22
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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