2-Nitroaniline → HCID 17810719, compound

HRID 916083Notes

Reaction equation

HRID 916083 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:25](C)=O.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.C(O)(=O)C>[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:25][NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:13]1

Participants

7

Reactant 4

HCID 69462-NitroanilineHCID 2671641-Methylindole-2-carboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17810719HCID 17810719, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-nitroaniline (829 mg, 6 mmol) and 1-methylindole carboxaldehyde (1242 mg, 7.8 mmol) were dissolved in 20 ml of tetrahydrofuran, to which acetic acid (200 μl) and NaBH(OAc)3 (5087 mg, 24 mmol) were sequentially added and stirred at room temperature overnight. A saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate, dried with anhydrous sodium sulfate, and the solvent was evaporated. After purification by silica gel column chromatography (hexane:ethyl acetate=95:5), ((1-methylindole-3-yl)methyl)(2-nitrophenyl)amine was obtained (264 mg, yield 18%).

Workup

  1. additionwere sequentially added
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialdried with anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customAfter purification by silica gel column chromatography (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-f623b876868f42718728c52ce13a47f9
Source dataset
uspto-grants-2007_09
Patent number
US07268145B2

Reaction notes

Loading…