Hydrochloric Acid → HCID 21884193, compound

HRID 722417Notes

Reaction equation

HRID 722417 reaction equation
[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=1.B.C1COCC1.Cl>C1COCC1>[CH2:14]([NH:13][C:6]1[CH:5]=[C:4]([CH2:3][NH:2][CH3:1])[CH:9]=[CH:8][C:7]=1[N+:10]([O-:12])=[O:11])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 218841793-(Butylamino)-N-methyl-4-nitrobenzamide

Product 1

HCID 21884193HCID 21884193, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-3-butylamino-4-nitrobenzamide (380 mg, 1.51 mmol) in anhydrous THF (20 mL) was added a solution of borane-THF (3.78 mL of a 2 M solution, 7.56 mmol) and the solution was stirred at room temperature 30 min, and then was warmed to reflux overnight. The solution was allowed to cool to room temperature, 1 N HCl was added to quench the reaction, and the aqueous was washed with ethyl acetate. The aqueous was made basic with 1 N NaOH and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated to give the product N-butyl-5-methylaminomethyl-2-nitroaniline (275 mg, 77%), approximately 90% pure by NMR and LCMS.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux overnight
  3. temperatureto cool to room temperature
  4. customto quench
  5. customthe reaction
  6. washthe aqueous was washed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0c6e50eb471445348fe76f7cba576e37
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Reaction notes

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