Formic Acid → 5-[[Formyl(methyl)amino]methyl]-2-nitro-benzoic acid
Reaction equation
[CH:1]([OH:3])=[O:2].C(O[C:8](=[O:10])C)(=O)C.C([O-])=O.[Na+].[CH3:15][NH:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:27]([O-:29])=[O:28])=[C:22]([CH:26]=1)C(O)=O>O>[CH:8]([N:16]([CH2:17][C:18]1[CH:26]=[CH:22][C:21]([N+:27]([O-:29])=[O:28])=[C:20]([CH:19]=1)[C:1]([OH:3])=[O:2])[CH3:15])=[O:10]Participants
Procedure
To a 100 mL volume egg plant-shaped flask, there were added 4.0 mL of formic acid and 2.7 mL of acetic anhydride and the mixture was stirred at room temperature. Subsequent to this, 0.65 g of sodium formate and 5.58 g (content: 71.7 wt %) of 5-(N-methyl-aminomethyl)-2-nitrobenzoic acid were added to the foregoing mixture in two portions and then the resulting mixture was stirred at room temperature for one hour. After the confirmation of the progress of the reaction by HPLC, 32 mL of water was added thereto to separate out crystals and to form a slurry and then cooled to 9° C. and stirred overnight. The solid separated out of the reaction liquid was filtered off, washed with water, dried under reduced pressure to thus obtain 3.95 g of the title compound as a white crystalline solid (yield: 87%).
Workup
- stirringthe resulting mixture was stirred at room temperature for one hour
- additionwas added
- customto separate out crystals
- customto form a slurry
- temperaturecooled to 9° C.
- stirringstirred overnight
- customThe solid separated out of the reaction liquid
- filtrationwas filtered off
- washwashed with water
Sources & evidence
- ORD record
- ord-622c825af6174ca48d36310d00aa535a
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546610B2
Reaction notes
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