Ammonium Chloride → HCID 90332507, compound

HRID 595590Notes

Reaction equation

HRID 595590 reaction equation
[Br:1][C:2]1[C:3]([N+:19]([O-])=O)=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:12][CH2:11]3)=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]=2[CH:18]=1.[NH4+].[Cl-]>CO.C1COCC1.O.[Fe]>[NH2:19][C:3]1[C:2]([Br:1])=[CH:18][C:6]2[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([CH:10]3[CH2:12][CH2:11]3)[O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90332499HCID 90332499, compound

Product 1

HCID 90332507HCID 90332507, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of crude compound ethyl 5-bromo-2-cyclopropyl-6-nitrobenzofuran-3-carboxylate (8.5 g, 25 mmol), iron filings (4.1 g, 75 mmol) and NH4Cl (8 g, 150 mmol) in MeOH-THF—H2O (2:2:1, 100 mL) were stirred at reflux for 3 hours. After being filtered and concentrated in vacuum, the residue was purified by column chromatography (eluted with PE:EA from 20:1 to 10:1) to furnish the pure product of ethyl 6-amino-5-bromo-2-cyclopropylbenzofuran-3-carboxylate (7.00 g, yield: 91%). 1H-NMR (400 MHz, CDCl3) δ 7.93 (s, 1H), 6.75 (s, 1H), 4.40 (q, J=7.2 Hz, 2H), 4.11 (s, 2H), 2.94˜2.99 (m, 1H), 1.43 (t, J=7.2 Hz, 3H), 1.19˜1.21 (m, 2H), 1.12˜1.15 (m, 2H). MS (M+H)+: 324/326.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationAfter being filtered
  3. concentrationconcentrated in vacuum
  4. customthe residue was purified by column chromatography (eluted with PE:EA from 20:1 to 10:1)

Sources & evidence

ORD record
ord-831f2ad0b3984b8381e1a9de16731673
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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