Ethanol → 2-amino-5-(1,4-dioxaspiro[4.5]dec-8-yl)-N-methylbenzamide

HRID 511341Notes

Reaction equation

HRID 511341 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:21][CH2:20][C:15]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:14][CH:13]=2)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].CCO.N#N>[Pd]>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:21][CH2:20][C:15]3([O:16][CH2:17][CH2:18][O:19]3)[CH2:14][CH2:13]2)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 947NitrogenHCID 672552222-amino-5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-methylbenzamide2×

Product 1

HCID 672539712-amino-5-(1,4-dioxaspiro[4.5]dec-8-yl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

10% Pd—C (50% H2O w/w) (264 mg, 0.124 mmol) was added to a solution of 2-amino-5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-methylbenzamide (Compound 139C, 357 mg, 1.24 mmol) in EtOH (30 mL, 500 mmol). The reaction mixture was subjected to three cycles of evacuation and N2 purging. After a fourth evacuation, the mixture was flushed with H2 and allowed to stirred under hydrogen overnight. The catalyst was removed by filtration through a pad of celite, and the filtrate was evaporated under reduced pressure to give the title compound as 333 mg of a pinkish solid. 1H NMR (400 MHz, DMSO-d6) δ 1.50-1.78 (m, 8H), 2.34-2.44 (m, 1H), 2.71 (d, J=4.55 Hz, 3H), 3.88 (t, J=2.40 Hz, 4H), 6.20 (s, 2H), 6.60 (d, J=8.34 Hz, 1H), 6.98 (dd, J=8.46, 1.89 Hz, 1H), 7.29 (d, J=2.02 Hz, 1H), 8.16 (d, J=4.55 Hz, 1H). MS (ES+): m/z=291.08 (100) [M+1]. HPLC: tR=2.60 min (ZQ3, polar—5 min).

Workup

  1. customAfter a fourth evacuation, the mixture was flushed with H2
  2. customThe catalyst was removed by filtration through a pad of celite
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-17b9c4df9be84783b909b21d4bfdb644
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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