Acetic Acid → HCID 69017759, compound

HRID 491628Notes

Reaction equation

HRID 491628 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.C[CH:14]=[CH:15][CH2:16][NH2:17].[CH3:18]C(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCO>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][NH:17][CH2:16][C:15]([CH3:18])=[CH2:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 304472-Buten-1-amineHCID 729332-Chloro-5-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69017759HCID 69017759, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-5-nitrobenzaldehyde (25 g) in EtOH (200 mL) was added 3-methylallylamine (10.6 g, 1.1 eq). HOAc (9 g) was added to the solution. The mixture was stirred at 20˜25° C. for 3 h. NaBH(OAc)3 (43 g, 1.5 eq) was added in one portion at ˜5° C. The mixture was warmed to RT in 30 min and stirred for 1 h. The EtOH was removed under reduced pressure and saturated Na2CO3 aqueous solution (200 mL) was added. The mixture was extracted with toluene (100 mL). To the toluene solution was added 5 N HCl in IPA (20 mL) at ˜5° C. in 1 h. The mixture was stirred for 1 h. The solids were filtered off, and dried under vacuum.

Workup

  1. stirringstirred for 1 h
  2. customThe EtOH was removed under reduced pressure and saturated Na2CO3 aqueous solution (200 mL)
  3. additionwas added
  4. extractionThe mixture was extracted with toluene (100 mL)
  5. additionTo the toluene solution was added 5 N HCl in IPA (20 mL) at ˜5° C. in 1 h
  6. stirringThe mixture was stirred for 1 h
  7. filtrationThe solids were filtered off
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3630207773a54fdea58703a2f942a7b4
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

Loading…