HCID 4447362, compound → 3-(1H-Benzimidazol-2-yl)-4-chloroaniline
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
Reactant 1
Product 1
Reagents, catalysts & solvents 3
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 nil). 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 redissolved 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 redissolved in CH2Cl2
- additionfew drops of hexane were added
- customto form a solid which
- customwas isolated by filtration
Sources & evidence
- ORD record
- ord-6376232c5f844bbd86858bf177d15412
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772275B2
Reaction notes
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