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

HRID 44477Notes

Reaction equation

HRID 44477 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-bb231810456e476a90f832b2c1aff03a
Source dataset
uspto-grants-2013_09
Patent number
US08541411B2

Reaction notes

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