Formic Acid → HCID 21088387, compound
Reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][OH:20].C(=O)([O-])O.[K+]>O1CCCC1>[OH:20][CH2:19][CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][CH:1]=[O:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
12.6 ml of formic acid were added dropwise at 0° C. to 15 ml of acetic anhydride, and the mixture was then stirred for 2 hours at 60° C. After cooling to 20° C., the mixture was diluted with 140 ml of tetrahydrofuran, cooled to −4° C., and at this temperature a solution of 18.4 g of 2-(2-aminophenyl)ethanol in 185 ml of tetrahydrofuran was added dropwise. After stirring for 3 hours at −6° C. the mixture was neutralised with aqueous potassium hydrogen carbonate solution (25% KHCO3) and extracted four times with 300 ml of ethyl acetate each time. The combined extracts were dried over sodium sulfate and concentrated by evaporation in vacuo. 18.4 g (94% of theory) of the title compound were thereby obtained in the form of yellowish crystals that melted at 49–54° C.
Workup
- temperatureAfter cooling to 20° C.
- temperaturecooled to −4° C.
- stirringAfter stirring for 3 hours at −6° C. the mixture
- extractionextracted four times with 300 ml of ethyl acetate each time
- dry with materialThe combined extracts were dried over sodium sulfate
- concentrationconcentrated by evaporation in vacuo
Sources & evidence
- ORD record
- ord-51ee964ad2ee4f0bb2b2ff761a5b33c9
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07183274B2
Reaction notes
Loading…