4-Aminobenzoic Acid → HCID 22045906, compound
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CN(C=O)C.[Br:16][CH2:17][C:18](Br)=[O:19]>O1CCOCC1>[Br:16][CH2:17][C:18]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-aminobenzoic acid (5.0 g, 36 mmol) in a mixture of anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) in a 250 mL 3-necked round-bottomed flask equipped with a constant addition funnel (60 mL) was cooled to 0° C. using an ice-bath. Bromoacetyl bromide (7.27 g, 3.16 mL, 36 mmol) was then added dropwise, keeping the internal temperature between 0° and 5° C. over a 1/2 h period. After the addition of the bromoacetyl bromide was completed, the solution was warmed to rt, stirred overnight, and then the solution was slowly poured into 500 mL of ice-water, causing a solid to precipitate. The precipitate was filtered, washed with water, and then dried in a vacuum dessicator overnight to afford 7.46 g (81%) of the title compound as a white solid, mp 241°-243° C.: 1H NMR (DMSO-d6) δ12.79 (bs, 1H), 10.68 (s, 1H), 7.91 (d, J=9.2, 2H), 7.69 (d, J=9.2, 2H), 4.06 (s, 2H); 13C NMR (DMSO-d6) δ166.79, 165.28, 142.56, 130.47, 125.70, 118.53, 30.29; MS (EI, m/z) 259 (M+).
Workup
- customequipped with a constant addition funnel (60 mL)
- customthe internal temperature between 0° and 5° C.
- customover a 1/2 h
- temperaturethe solution was warmed to rt
- customto precipitate
- filtrationThe precipitate was filtered
- washwashed with water
- customdried in a vacuum dessicator overnight
Sources & evidence
- ORD record
- ord-e24770b3e0524ab8aa7bf1defc192114
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05741926
Reaction notes
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