HCID 4447362, compound → 3-(1H-Benzimidazol-2-yl)-4-chloroaniline

HRID 1803831Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)=O>C1(C)C=CC=CC=1.C(O)(=O)C.[Fe]>[NH:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:13]=[C:4]1[C:3]1[CH:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 125 °C

Procedure

Iron powder (15.42 g, 280 mmol) was added to a solution of amide 1 (15.00 g, 46.7 mmol) in toluene (125 ml) and acetic acid (60 ml). The mixture was heated at 125° C. for about 1 h (completion of the reaction was monitored by LCMS) and the resulting crude mixture was filtered through a cotton wool plug (to remove iron particles). The crude solution was evaporated to dryness, diluted with EtOAc, washed with saturated NaHCO3 then brine, dried over MgSO4, filtered, and concentrated at reduced pressure. The resulting brown solid was re-dissolved in CH2Cl2 and few drops of hexane were added to form a solid which was isolated by filtration to give 2 (5.66 g, 42%) as a beige solid: 1H NMR (CD3OD) δ 7.64 (broad s, 2H), 7.30-7.26 (m, 3H), 7.13 (app d, 1H), 6.84 (dd, 1H); MS (ES, positive mode): 244 [M++1].

Workup

filtrationwas filtered through a cotton wool plug (to remove iron particles)
customThe crude solution was evaporated to dryness
additiondiluted with EtOAc
washwashed with saturated NaHCO3
dry with materialbrine, dried over MgSO4
filtrationfiltered
concentrationconcentrated at reduced pressure
dissolutionThe resulting brown solid was re-dissolved in CH2Cl2
additionfew drops of hexane were added
customto form a solid which
customwas isolated by filtration

Sources & evidence

ORD record: ord-f6e20cab3e76452087cf961cd47ad9f9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354397B2

Reaction notes

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