Dichloromethane → 2-Cyclopropyl-7-iodo-1-benzofuran-5-amine

HRID 575841Notes

Reaction equation

HRID 575841 reaction equation
[CH:1]1([C:4]2[O:5][C:6]3[C:12]([I:13])=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:7]=3[CH:8]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-].C(Cl)Cl>CO.[Fe]>[CH:1]1([C:4]2[O:5][C:6]3[C:12]([I:13])=[CH:11][C:10]([NH2:14])=[CH:9][C:7]=3[CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 1180218282-Cyclopropyl-7-iodo-5-nitrobenzofuran

Product 1

HCID 1180222192-Cyclopropyl-7-iodo-1-benzofuran-5-amineYield 83.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of the title compound from Step 1 (2.0 g, 6.0 mmol) and Fe (1.0 g, 18 mmol) in MeOH (80 mL) was added sat. NH4Cl solution (10 mL). The reaction mixture was refluxed for 1 h. The mixture was cooled to room temperature and poured into 400 mL of DCM. The resulting mixture was filtered and the filtrate was washed with water (100 mL) and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude title compound (1.5 g, 83% yield) as red oil that was used for the next step directly. 1H NMR (CDCl3, 400 MHz): δ 6.87 (d, J=2.4 Hz, 1H), 6.61 (d, J=2.0 Hz, 1H), 6.19 (s, 1H), 3.45 (br, 2H), 1.97-1.90 (m, 1H), 0.95-0.85 (m, 4H). LCMS: 300 (M+1)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. filtrationThe resulting mixture was filtered
  3. washthe filtrate was washed with water (100 mL) and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef2f54e553c2425197dd499286f5d804
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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