N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide → 4-(7-methoxy-2-methyl-3H-benzo[d]imidazol-5-yl)morpholine

HRID 1188778Notes

Reaction equation

HRID 1188778 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[C:5]([N+:15]([O-])=O)[C:4]=1[NH:18][C:19](=O)[CH3:20]>CC(O)=O.[Fe]>[CH3:1][O:2][C:3]1[C:4]2[N:18]=[C:19]([CH3:20])[NH:15][C:5]=2[CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=1

Participants

4

Reactant 1

HCID 66977019N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide

Product 1

HCID 669771484-(7-methoxy-2-methyl-3H-benzo[d]imidazol-5-yl)morpholineYield 100.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a refluxing solution of combined batches of N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide (2.06 g) in HOAc (60 mL) was added iron powder (1.18 g) and the mixture was stirred at reflux temperature overnight. It was cooled to room temperature and filtered. The filtrate was concentrated in-vacuo and the residue was washed with EtOAc:petroleum ether=1:1 to afford crude product as a solid (1.73 g, 100%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.56 (s, 3H), 3.12 (t, 4H, J=4.8 Hz), 3.88 (t, 4H, J=4.8 Hz), 3.94 (s, 3H), 6.39 (s, 1H), 6.62 (s, 1H); LC-MS: m/e=248 [M+1]+

Workup

  1. temperatureat reflux temperature overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in-vacuo
  4. washthe residue was washed with EtOAc

Sources & evidence

ORD record
ord-0cc34f4420f54b1e8b3443c73cb0afc5
Source dataset
uspto-grants-2014_03
Patent number
US08674090B2

Reaction notes

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