Ammonium Chloride → Ethyl 1-((2-amino-5-bromophenylamino)methyl)cyclopropanecarboxylate

HRID 1485428Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Iron powder (448 mg, 8.0 mmol) was added to a mixture of ethyl 1-((5-bromo-2-nitrophenylamino)methyl)cyclopropanecarboxylate (684 mg, 2.0 mmol), ammonium chloride aqueous (6 mL) and ethanol (20 mL). The reaction was heated to 70° C. and maintained at the 70° C. for 2 hours. The mixture solution was filtered. The filtrate was evaporated, diluted with water (100 mL), extracted with ethyl acetate (100 mL), and dried by sodium sulfate. The mixture was filtered. The filtrate was concentrated and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give ethyl 1-((2-amino-5-bromophenylamino)methyl)cyclopropanecarboxylate (474 mg, 76%) as off-white solid.

Workup

temperaturemaintained at the 70° C. for 2 hours
filtrationThe mixture solution was filtered
customThe filtrate was evaporated
additiondiluted with water (100 mL)
extractionextracted with ethyl acetate (100 mL)
dry with materialdried by sodium sulfate
filtrationThe mixture was filtered
concentrationThe filtrate was concentrated
custompurified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record: ord-1dd255f9f9054a94a932c20a92f230d2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422292B2

Reaction notes

Loading…