Ammonia → HCID 81430592, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5](O)=[O:6].O=S(Cl)Cl.[NH3:19]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5](=[O:6])[NH2:19])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 3-bromo-5-methoxycarbonyl-benzoic acid (3 g, 11.6 mmol, 1 eq) was added SOCl2 (20 mL) and the reaction heated at reflux overnight. The excess SOCl2 was removed in vacuo and the residue obtained was dissolved in THF (15 mL) and added dropwise to a solution of NH3 (38% aqueous, 30 mL). The precipitate that formed was collected by filtration, washed with water and dried to give the title compound as a white solid (2.8 g, 94%).
Workup
- temperaturethe reaction heated
- temperatureat reflux overnight
- customThe excess SOCl2 was removed in vacuo
- customthe residue obtained
- customThe precipitate that formed
- filtrationwas collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-d8820c0f221b4cf49ec566a59d595dc0
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249085B2
Reaction notes
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