Hydrochloric Acid → 2,5-Diamino-3-chlorobenzonitrile

HRID 905568Notes

Reaction equation

HRID 905568 reaction equation
Cl.[NH2:2][C:3]1[C:10]([Cl:11])=[CH:9][C:8]([N+:12]([O-])=O)=[CH:7][C:4]=1[C:5]#[N:6].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.[Zn]>[NH2:2][C:3]1[C:10]([Cl:11])=[CH:9][C:8]([NH2:12])=[CH:7][C:4]=1[C:5]#[N:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 88504Benzonitrile, 2-amino-3-chloro-5-nitro-

Product 1

HCID 137997002,5-Diamino-3-chlorobenzonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous hydrochloric acid (12 M, 5.3 mL) was added slowly to a mixture of zinc dust (2.01 g) and 2-amino-3-chloro-5-nitro-benzonitrile (0.50 g) in tetrahydrofuran (40 mL). The reaction mixture was stirred for 2 hours, neutralized with saturated aqueous sodium carbonate (50 mL), and extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over sodium sulfate and concentrated in vacuo to furnish 0.42 g (99% yield) of the title compound as a red solid. 1H NMR (500 MHz, DMSO-d6): 4.89 (s, 2H), 5.13 (s, 2H), 6.64 (d, 1H), 6.89 (d, 1H).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f672828366f74d88a7e38434c4f14002
Source dataset
uspto-grants-2011_09
Patent number
US08012962B2

Reaction notes

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