Water → 4-(4-Bromo-imidazol-1-yl)-3-methoxy-phenylamine

HRID 604924Notes

Reaction equation

HRID 604924 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[O:16][CH3:17])[CH:6]=1.O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(O)C>[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=2[O:16][CH3:17])[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 668864944-bromo-1-(2-methoxy-4-nitro-phenyl)-1H-imidazole

Product 1

HCID 668852504-(4-Bromo-imidazol-1-yl)-3-methoxy-phenylamineYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

700 mg (2.35 mmol) 4-bromo-1-(2-methoxy-4-nitro-phenyl)-1H-imidazole and 2.755 g (12.2 mmol) stannous chloride dihydrate were suspended in a mixture of 40 ml ethyl acetate and 10 ml ethanol and stirred for 1 h at 70° C. The resulting mixture was poured into cold water and neutralized by addition of a saturated solution of sodium hydrogen carbonate. The product was extracted with ethyl acetate, dried and evaporated to give 627 mg (100%) of 4-(4-bromo-imidazol-1-yl)-3-methoxy-phenylamine as a yellowish solid. MS ISP (m/e): 268.0/270.1 (100/82) (M+H)+. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.49 (s, 1H), 7.77 (s, 1 H), 7.05 (s, 1H), 6.99 (d, 2H), 6.35-6.25 (m, 2H), 3.86 (s broad, 2H), 3.77 (s, 3H).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-1e403577dc7c468fb108fd0b3780c766
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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