4-Hydrazinobenzoic acid → HCID 22170448, compound
Reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].C(O[CH:15]=[CH:16][C:17](=O)[C:18]([F:21])([F:20])[F:19])C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>CCO.C(Cl)(Cl)Cl>[F:19][C:18]([F:21])([F:20])[C:17]1[N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=2)[N:2]=[CH:15][CH:16]=1Participants
7
Conditions
- Temperature
- 75 °C
Procedure
A mixture of 4-hydrazinobenzoic acid (0.501 g, 3.29 mmol) and 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (0.48 mL, 3.4 mmol) in EtOH (15 mL) was heated to 75° C. for 17 hours, allowed to cool to room temperature, and concentrated under reduced pressure to provide a solid. The obtained solid was suspended in CHCl3 (15 mL), treated with P2O5 (0.50 g, 3.5 mmol), and heated at 65° C. for 6 hours. After cooling to room temperature, the mixture was treated with 1N NaOH (5 mL) and stirred for 30 minutes. The mixture was quenched with 1N HCl (6 mL) and extracted with CH2Cl2 (3×8 mL). The extracts were combined, dried (Na2SO4), filtered, and the filtrate concentrated to provide the title compound as a solid.
Workup
- temperatureto cool to room temperature
- concentrationconcentrated under reduced pressure
- customto provide a solid
- temperatureheated at 65° C. for 6 hours
- temperatureAfter cooling to room temperature
- customThe mixture was quenched with 1N HCl (6 mL)
- extractionextracted with CH2Cl2 (3×8 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationthe filtrate concentrated
Sources & evidence
- ORD record
- ord-07d8d02450204514b821e7fa94b69376
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595332B2
Reaction notes
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