N-Methylbenzeneethanamine → HCID 117701876, compound

HRID 1751962Notes

Reaction equation

HRID 1751962 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[CH2:8][CH2:9][C:10](=O)[CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].[CH3:15][NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH3:15][N:16]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:10]1[CH2:9][CH2:8][C:7]2[N:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:12]=2[CH2:11]1

Participants

6

Reactant 4

HCID 11503N-MethylbenzeneethanamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 55263195HCID 55263195, compound

Product 1

HCID 117701876HCID 117701876, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A100 mL flask, equipped with a magnetic stirbar, was charged with 3-nitro-7,8-dihydroquinolin-6(5H)-one (2.5 g, 13.0 mmol), N-methyl-2-phenylethanamine (1.76 g, 13.0 mmol), and 1,2-dichloroethane (73 mL). Sodium triacetoxyborohydride (4.13 g, 19.5 mmol) was added as a solid. The mixture was stirred at ambient temperature for 40 hours. Saturated NaHCO3 (aq) was added until the pH=8. The mixture was extracted with dichloromethane (3×50 mL). The combined organic portions were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (0 to 10% MeOH in dichloromethane) to provide the title compound (0.73 g, 18%). 1H NMR (400 MHz, CD3OD), δ9.16 (d, 1H, J=2.6), 8.13 (d, 1H, J=2.6), 7.30-7.17 (m, 5H), 3.19 (ddd, 2H, J=19, 6, 4), 2.96-2.89 (m, 6H), 2.45 (s, 3H), 2.21-2.12 (m, 2H), 1.89-1.84 (m, 1H). MS [M+H]+=312.2 m/z.

Workup

  1. customA100 mL flask, equipped with a magnetic stirbar
  2. extractionThe mixture was extracted with dichloromethane (3×50 mL)
  3. dry with materialThe combined organic portions were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0 to 10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-fb986a47807b45cfae3f29a25e14c8b5
Source dataset
uspto-grants-2015_10
Patent number
US09162983B2

Reaction notes

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