Methanol → 5-(methyloxy)-1-[(methyloxy)acetyl]-2,3-dihydro-1H-indol-6-amine

HRID 1014276Notes

Reaction equation

HRID 1014276 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[N:8]([C:15](=[O:19])[CH2:16][O:17][CH3:18])[CH2:7][CH2:6]2.CO.[BH4-].[Na+]>C1COCC1.Cl[Ni]Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[NH2:12])[N:8]([C:15](=[O:19])[CH2:16][O:17][CH3:18])[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 594420105-(methyloxy)-1-[(methyloxy)acetyl]-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 594417515-(methyloxy)-1-[(methyloxy)acetyl]-2,3-dihydro-1H-indol-6-amineYield 25.2%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 5-(methyloxy)-1-[(methyloxy)acetyl]-6-nitro-2,3-dihydro-1H-indole (3.96 g, 14.87 mmol) and NiCl2 6H2O (1.061 g, 4.46 mmol) in THF (50 mL) and MeOH (100 mL) was treated with NaBH4 (1.69 g, 44.6 mmol) in small portions. After 5 minutes the reaction mixture was concentrated onto Celite and purified by silica gel chromatography using THF. The crude product was triturated using CH2Cl2 and Et2O to obtain 5-(methyloxy)-1-[(methyloxy)acetyl]-2,3-dihydro-1H-indol-6-amine as a white solid (884 mg, 25%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.98 (t, J=8.24 Hz, 2H), 3.34 (s, 3H), 3.71 (s, 3H), 3.93 (t, J=8.,33 Hz 2H), 4.12 (s, 2H), 4.67 s, 2H), 6.71 (s, 1H), 7.54 (s, 1H); ESIMS (M+H)+=237.4.

Workup

  1. concentrationAfter 5 minutes the reaction mixture was concentrated onto Celite
  2. custompurified by silica gel chromatography
  3. customThe crude product was triturated

Sources & evidence

ORD record
ord-1d5f928b240648b88cebd623e7637504
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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