Hydrochloric Acid → 3-Amino-5-bromo-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)benzamide

HRID 1423253Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([N+:21]([O-])=O)[CH:20]=1)[C:5]([NH:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])=[O:6].Cl>CCO.O.[Fe]>[NH2:21][C:19]1[CH:18]=[C:4]([CH:3]=[C:2]([Br:1])[CH:20]=1)[C:5]([NH:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])=[O:6]

Participants

Conditions

Temperature: 75 °C

Procedure

Iron powder (5.90 g, 106 mmol) was added to a solution of the product from step (i) above (8.24 g, 20.43 mmol) and concentrated HCl (2 mL, 23.40 mmol) in EtOH (65 mL) and water (15 mL). The mixture was heat at 75° C. (block temperature) for 1 h. Then, the reaction was cooled to rt, before being diluted with water (30 mL), filtered and concentrated in vacuo. The residue was basified (NaHCO3) then partitioned between EtOAc (350 mL) and water (275 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford an orange oil that was purified by chromatography on silica gel (220 g column, 0-5% MeOH in DCM) to afford the sub-title compound (5.25 g) as an orange oil.

Workup

temperatureThen, the reaction was cooled to rt
filtrationfiltered
concentrationconcentrated in vacuo
customthen partitioned between EtOAc (350 mL) and water (275 mL)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto afford an orange oil that
customwas purified by chromatography on silica gel (220 g column, 0-5% MeOH in DCM)

Sources & evidence

ORD record: ord-752283ff001647cbbfb4634ec2d6e16d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927563B2

Reaction notes

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