4-Methoxybenzoic Acid → HCID 67079010, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[CH:7][CH:8]=1.[C:12](Cl)(=O)C(Cl)=O.CCl.[NH2:20][CH2:21][C:22](=[O:28])[CH2:23][CH2:24][C:25]([OH:27])=[O:26].C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:12][O:26][C:25](=[O:27])[CH2:24][CH2:23][C:22]([CH2:21][NH:20][C:9](=[O:11])[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:28]Participants
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere, a catalytic amount of dimethylformamide was added to a solution of p-methoxybenzoic acid (5 g, 33.0 mmol) in dichloromethane (50 mL), and the obtained mixture was then cooled to 0° C. Thereafter, oxalyl chloride (5.8 mL, 66.1 mmol) was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 30 minutes. Thereafter, the solvent was distilled away, and the obtained residue was then added to a solution of 5-aminolevulinic acid methyl hydrochloride (1.0 g, 5.50 mmol) and triethylamine (2.3 mL, 16.5 mmol) in dichloromethane (80 mL) that had been cooled to 0° C. under a nitrogen atmosphere. The obtained mixture was stirred at room temperature for 3 hours. Thereafter, the solvent was distilled away, and the obtained residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain the title compound (6.46 g, yield: 84%).
Workup
- distillationThereafter, the solvent was distilled away
- temperaturehad been cooled to 0° C. under a nitrogen atmosphere
- stirringThe obtained mixture was stirred at room temperature for 3 hours
- distillationThereafter, the solvent was distilled away
- customthe obtained residue was then purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-9458113e91824acb9235bf263731a526
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150563B2
Reaction notes
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