Propanal → HCID 16081264, compound

HRID 2294977Notes

Reaction equation

HRID 2294977 reaction equation
C([BH3-])#N.[Na+].[I:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1.[CH:13](=O)[CH2:14][CH3:15]>CO>[CH2:13]([NH:10][C:9]1[CH:11]=[CH:12][C:6]([I:5])=[CH:7][CH:8]=1)[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 527PropanalHCID 108934-IodoanilineHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 16081264HCID 16081264, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.63 g) was added to a solution of 4-iodoaniline (2.2 g) and propionaldehyde (0.72 ml) in methanol (15 ml) whilst under an atmosphere of argon. The mixture was stirred at ambient temperature for 72 hours. Sodium cyanoborohydride (0.005 mole) was added and the reaction mixture was stirred for further 48 hours. The pH of the reaction mixture was adjusted to 1 using 2N aqueous hydrocyloric acid. The mixture was filtered and the filtrate was evaporated to yield N-propyl-4-iodoaniline as a solid (1.4 g), NMR: 0.9(3H,t), 1.65(2H,m), 3.1(2H,m), 7.05(2H,d) and 7.67(2H,d).

Workup

  1. stirringthe reaction mixture was stirred for further 48 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f8e6034babad4b7dbec6d0ff53a93f78
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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