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

HRID 2174746Notes

Reaction equation

HRID 2174746 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-6a5b286153b14121b46f456bfab0a9c7
Source dataset
uspto-grants-2015_06
Patent number
US09062003B2

Reaction notes

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