Aniline → HCID 67452579, compound

HRID 2175457Notes

Reaction equation

HRID 2175457 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2[CH:7]=[C:8]([CH:11]=O)[CH:9]=[CH:10][C:4]=2[O:3]1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH3-][C:22]#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH3:13][C:2]1([CH3:1])[CH:6]=[CH:22][C:5]2[C:4](=[CH:10][CH:9]=[C:8]([CH2:11][NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:7]=2)[O:3]1

Participants

6

Reactant 3

HCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 223443542,2-Dimethyl-2,3-dihydro-1-benzofuran-5-carbaldehyde

Product 1

HCID 67452579HCID 67452579, compoundYield 111%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,3-dihydro-2,2-dimethylbenzofuran-5-carboxaldehyde 14 (250 mg, 1.42 mmol) in MeOH (10 mL) was added aniline (0.14 mL, 1.022 mmol), NaCNBH3 (178 mg, 2.84 mmol) and ZnCl2 (dried in oven) (387 mg, 2.84 mmol). The reaction was stirred at room temperature overnight, and then the solvent was removed by rotary evaporation. 0.1M NaOH was added to the resulting residue, which was extracted with EtOAc (×2). The combined organic layers were dried over MgSO4 and concentrated in vacuum to give 301 mg of the product (84%). 1H NMR (CDCl3): d 7.29-7.22 (m, 3H), 7.17 (d, J=8.0 Hz, 1H), 6.95-6.70 (m, 4H), 4.28 (s, 2H), 3.06 (s, 2H), 1.55 ppm (s, 6H).

Workup

  1. customthe solvent was removed by rotary evaporation
  2. addition0.1M NaOH was added to the resulting residue, which
  3. extractionwas extracted with EtOAc (×2)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-32b3c39128b04cf5b117fca7d3823d07
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

Loading…