2-Nitrophenol → HCID 58272777, compound

HRID 331209Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=CC(OC)=[C:9](OC)[CH:10]=2)N=CC=1.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1O)([O-:18])=[O:17].CN(C1C=CC=CN=1)C.[N:35]1[C:40](C)=[CH:39][CH:38]=[CH:37][C:36]=1[CH3:42].C(=O)([O-])[O-:44].[K+].[K+]>O.CO>[CH3:6][C:11]1[CH:2]=[C:37]2[C:36](=[CH:42][C:10]=1[CH3:9])[N:35]=[CH:40][CH:39]=[C:38]2[O:44][C:22]1[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 147 °C

Procedure

A reactor was sequentially charged with 4-chloro-6,7-dimethoxy-quinoline (8.0 kg), 4 nitrophenol (7.0 kg), 4 dimethylaminopyridine (0.9 kg), and 2,6 lutidine (40.0 kg). The reactor contents were heated to approximately 147° C. When the reaction was complete (<5% starting material remaining as determined by in process HPLC analysis, approximately 20 hours), the reactor contents were allowed to cool to approximately 25° C. Methanol (26.0 kg) was added, followed by potassium carbonate (3.0 kg) dissolved in water (50.0 kg). The reactor contents were stirred for approximately 2 hours. The resulting solid precipitate was filtered, washed with water (67.0 kg), and dried at 25° C. for approximately 12 hours to afford the title compound (4.0 kg).

Workup

custom(<5% starting material remaining as determined by in process HPLC analysis, approximately 20 hours)
temperatureto cool to approximately 25° C
filtrationThe resulting solid precipitate was filtered
washwashed with water (67.0 kg)
customdried at 25° C. for approximately 12 hours

Sources & evidence

ORD record: ord-b17feaa2556748a28d44715929105f94
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877776B2

Reaction notes

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