Ammonia → 4-Nitroindazole

HRID 1790081Notes

Reaction equation

HRID 1790081 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[N:12]([O-])=O.[Na+].N>O.C(O)(=O)C.C(OCC)(=O)C>[N+:9]([C:8]1[CH:7]=[CH:6][CH:5]=[C:3]2[C:2]=1[CH:1]=[N:12][NH:4]2)([O-:11])=[O:10]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 117832-Methyl-3-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 180574-Nitroindazole

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-methyl-3-nitro-aniline (5.00 g, 32.9 mmol) and a solution of sodium nitrite (2.27 g, 32.9 mmol) in water (7.5 mL) in glacial acetic acid (750 mL) was was stirred for 15 minutes and allowed to stand at room temperature for 3 days. The mixture was concentrated under reduced pressure leaving a pale yellow solid which was dissolved in ethyl acetate (250 mL) and filtered through a plug of silica gel, rinsing with ethyl acetate. The combined ethyl acetate was concentrated under reduced pressure to provide a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.65 (m, 1H), 8.10 (m, 1H), 8.16 (m, 1H), 8.54 (s, 1H), 13.9 (s, 1H); MS (DCI/NH3) m/z 164 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customleaving a pale yellow solid which
  3. filtrationfiltered through a plug of silica gel
  4. washrinsing with ethyl acetate
  5. concentrationThe combined ethyl acetate was concentrated under reduced pressure
  6. customto provide a pale yellow solid

Sources & evidence

ORD record
ord-3603a9eb0c3044cab88c5864caa24b95
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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