Hydrochloric Acid → HCID 178507473, compound

HRID 1354800Notes

Reaction equation

HRID 1354800 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[N-:13]=[N+:14]=[N-:15].[Na+].Cl>[Zn+2].[Br-].[Br-]>[N+:10]([C:3]1[CH:4]=[C:5]([C:6]2[NH:15][N:14]=[N:13][N:7]=2)[CH:8]=[CH:9][C:2]=1[NH2:1])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 5959014-Amino-3-nitrobenzonitrile

Product 1

HCID 178507473HCID 178507473, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

A mixture of 4-amino-3-nitrobenzonitrile (8-1) (163 mg, 1.0 mmol), NaN3 (1.5 mL of 2.0 M solution, 3.0 mmol) ZnBr2 (1.0 mL of 2.0 M solution, 2.0 mmol) was microwaved (Smith-Synthesizer) at 160° C. for 15 min with stirring. After this time, the reaction was completion according to LCMS. The reaction mixture was acidified to pH=2 with concentrated HCl. The precipitated product was collected by filtration and washed with water (2×3 mL). After drying, 179 mg (87%) of desired product were obtained as a yellow solid. Analytical LCMS: single peak, (214 nm), 1.909 min; 1H NMR (500 MHz, DMSO-d6): δ 8.70 (d, J=2.0 Hz, 1H), 8.02 (dd, J=8.9, 2.0 Hz, 1H), 7.92 (s, 2H), 7.21 (d, J=8.9 Hz, 1H).

Workup

  1. customwas microwaved (Smith-Synthesizer) at 160° C. for 15 min
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed with water (2×3 mL)
  4. customAfter drying

Sources & evidence

ORD record
ord-d84606aff09f45de94ca327f2ab3d3c3
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

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