HCID 117843538, compound → HCID 117842880, compound

HRID 2209037Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

4-bromo-N-cyclopropyl-2-methoxy-6-nitroaniline (1.05 g, 3.66 mmol) and iron powder (1.43 g, 25.6 mmol) were suspended in ethanol (19 mL) and acetic acid (9.5 mL). The stirred mixture was heated to 60° C. for 1 h and was diluted with EtOH (20 mL EtOH). Celite (15 g) was added and the mixture was filtered through a pad of Celite with EtOH. The filtrated was concentrated in vacuo. The crude residue was taken up in and concentrated once from 30 mL EtOH to afford crude 4-bromo-N1-cyclopropyl-6-methoxybenzene-1,2-diamine that was used immediately in the following step. LCMS-ESI+ (m/z): [M+H]+ calcd for C10H14BrN2O: 257.03; found: 257.15.

Workup

additionCelite (15 g) was added
filtrationthe mixture was filtered through a pad of Celite with EtOH
concentrationThe filtrated was concentrated in vacuo
concentrationconcentrated once from 30 mL EtOH

Sources & evidence

ORD record: ord-8b67ad9ead3245d999b027a847058a0d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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