Oxalic acid dihydrate → HCID 21189943, compound
Reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][C:5]([Br:10])=[CH:4][C:3]=1[NH2:11].O.O.[C:14](O)(=[O:18])[C:15](O)=[O:16]>Cl.[OH-].[Na+]>[Br:10][C:5]1[CH:4]=[C:3]2[C:2]([NH:1][C:14](=[O:18])[C:15](=[O:16])[NH:11]2)=[C:7]([CH2:8][CH3:9])[CH:6]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 62.5 °C
Procedure
A mixture of 1,2-diamino-4-bromo-6-ethylbenzene (40 mg, 0.14 mmol) and oxalic acid dihydrate (25 mg, 0.20 mmol, used as received) in 4 N HCl (1.5 mL) was refluxed at 120-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed with cold water (2×1 mL), collected by filtration, and dried at 60° C. under reduced pressure for 2 h, affording 40 mg of crude product (80%) as a yellow powder. The crude product was dissolved in 1N NaOH (2 mL) and filtered. The filtrate was acidified to pH=5, affording 12 mg of pure title compound; mp:>350° C. (dec. from 300° C.); IR (KBr, cm-1):3410, 3164, 2919, 1740, 1705, 1600. 1H NMR (DMSO-d6): δ 1.099 (t, 3 H, J=6 Hz), 2.741 (q, 2 H, J=7.2 Hz), 7.117 (d, 1 H, J=1.8 Hz), 7.138 (d, 1 H, J=1.8 Hz); 11.343 (s, 1H); 11.958 (s, 1H). HRMS: calcd for C10H9BrN2O2 (M+) m/z: 267.9846; found 267.9853.
Workup
- temperaturecooled to room temperature
- customthe liquid layer was removed
- washThe yellow solid was washed with cold water (2×1 mL)
- filtrationcollected by filtration
- customdried at 60° C. under reduced pressure for 2 h
- customaffording 40 mg of crude product (80%) as a yellow powder
- filtrationfiltered
Sources & evidence
- ORD record
- ord-975c28bb400b41f2b09b64393057832e
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147075
Reaction notes
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