Hydrochloric Acid → 2-Methyl-4-(2-nitrobenzylamino)butanol

HRID 553404Notes

Reaction equation

HRID 553404 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[NH2:12][CH2:13][CH2:14][CH:15]([CH3:18])[CH2:16][OH:17].[BH4-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:18][CH:15]([CH2:14][CH2:13][NH:12][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:16][OH:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 4311764Sodium borohydrideHCID 101299114-Amino-2-methyl-1-butanol

Product 1

HCID 674613512-Methyl-4-(2-nitrobenzylamino)butanolYield 96.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Nitrobenzaldehyde (7.33 g, 48.5 mmol) and 4-amino-2-methylbutanol (5.00 g, 48.5 mmol) were dissolved in toluene (50 ml) and heated to reflux for two hours with Dean Stark dehydration apparatus. After allowed to cool, the solvent was evaporated under reduced pressure. The obtained concentrate was dissolved in methanol (100 ml), added with sodium borohydride (2.75 g, 72.8 mmol) under ice cooled condition and stirred at the same temperature for two hours. The reaction mixture was further stirred at room temperature for two hours, adjusted to pH 4 by adding 1N hydrochloric acid, and the solvent was evaporated under reduced pressure. Water (30 ml) was added to dissolve the concentrate and after extracted with ethyl acetate, pH was adjusted to 8 by added a saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain 2-methyl-4-(2-nitrobenzylamino)butanol (11.12 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for two hours with Dean Stark dehydration apparatus
  3. temperatureto cool
  4. customthe solvent was evaporated under reduced pressure
  5. concentrationThe obtained concentrate
  6. dissolutionwas dissolved in methanol (100 ml)
  7. stirringThe reaction mixture was further stirred at room temperature for two hours
  8. customthe solvent was evaporated under reduced pressure
  9. additionWater (30 ml) was added
  10. dissolutionto dissolve the
  11. concentrationconcentrate
  12. extractionafter extracted with ethyl acetate, pH
  13. additionby added a saturated sodium hydrogen carbonate aqueous solution
  14. extractionextracted with ethyl acetate
  15. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  16. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9c5e9dd9f0e04c4ea754d9a84936acdd
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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