Hydrochloric Acid → HCID 12897331, compound
Reaction equation
Cl.[Cl:2][C:3]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([N+:14]([O-])=O)=[CH:7][C:4]=1[C:5]#[N:6].[OH-].[Na+]>>[Cl:2][C:3]1[C:10]([NH2:11])=[CH:9][C:8]([NH2:14])=[CH:7][C:4]=1[C:5]#[N:6]Participants
Procedure
To a solution of 19- gm. (0.86 mole) of stannous chloride dihydrate in 475 ml. of concentrated hydrochloric acid is added 27.5 gm. (0.12 mole) of 2-chloro-3,5-dinitrobenzonitrile. The temperature rises to 84° and a solution occurs. The mixture is allowed to cool to room temperature, placed in an ice-bath, cooled to 0° and a cold 50% sodium hydroxide solution is added, with cooling, until the mixture is strongly basic. The gelatinous precipitate is removed by filtration. The precipitate is washed thoroughly (4 times) with portions of ethyl acetate. The combined ethyl acetate washes are used to extract the aqueous filtrate. The combined ethyl acetate extracts are dried over anhydrous MgSO4 and the solvent removed by distillation. The residue is recrystallized for ethanol. There is obtained 11.30 gm. (56%) of colorless needles melting at 181°-82°.
Workup
- customrises to 84°
- customplaced in an ice-bath
- temperaturecooled to 0°
- temperaturewith cooling, until the mixture
- customThe gelatinous precipitate is removed by filtration
- washThe precipitate is washed thoroughly (4 times) with portions of ethyl acetate
- extractionto extract the aqueous filtrate
- dry with materialThe combined ethyl acetate extracts are dried over anhydrous MgSO4
- customthe solvent removed by distillation
- customThe residue is recrystallized for ethanol
- customThere is obtained 11.30 gm
Sources & evidence
- ORD record
- ord-bdcd21b3d4ba464ba0fe627d1ff3111c
- Source dataset
- uspto-grants-1979_06
- Patent number
- US04159278
Reaction notes
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