Anthranilic Acid → HCID 18174482, compound
Reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11]([C:15]1[CH:23]=[CH:22][C:18](C(Cl)=O)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].Cl.N1C=CC=C[CH:26]=1>>[C:11]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:22][C:23]=1[C:26]1[O:9][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[N:4]=1)([CH3:12])([CH3:13])[CH3:14]Participants
Procedure
To a stirred solution of anthranilic acid (34.3 g, 250 mmol) in pyridine (400 mL) was added 4-tert-butylbenzoyl chloride (94 mL, 500 mL) dropwise via an addition funnel. After stirring for 12 h, the solution was poured onto a slurry of ice and 2 N aqueous hydrochloric acid (100 mL). The mixture was extracted with dichloromethane and the organic extract was concentrated in vacuo. The residue was dissolved in fresh dichloromethane, washed once with 2 N aqueous hydrochloric acid, once with saturated aqueous sodium chloride solution, twice with saturated aqueous sodium bicarbonate solution, three times with water, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was crystallized from ether/hexanes to give an initial crop of 15.2 g (22%) of the title compound as an off-white solid, followed by additional crops totalling 16.9 g (24%).
Workup
- extractionThe mixture was extracted with dichloromethane
- extractionthe organic extract
- concentrationwas concentrated in vacuo
- dissolutionThe residue was dissolved in fresh dichloromethane
- washwashed once with 2 N aqueous hydrochloric acid, once with saturated aqueous sodium chloride solution, twice with saturated aqueous sodium bicarbonate solution, three times with water
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was crystallized from ether/hexanes
Sources & evidence
- ORD record
- ord-4c53b5ba752d4dba8fe1850b62c7639b
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06605626B2
Reaction notes
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