Ammonia → 4-Nitroindazole

HRID 1825814Notes

Reaction equation

HRID 1825814 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>C(O)(=O)C.O.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 solution of 2-methyl-3-nitro-aniline (5.00 g, 32.9 mmol) in glacial acetic acid (750 mL) was treated with a solution of sodium nitrite (2.27 g, 32.9 mmol) in water (7.5 mL). The resultant solution was stirred for 15 minutes and allowed to stand at room temperature for 3 days. The acetic acid was removed in vacuo, 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 ethyl acetate was removed in vacuo to afford a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.65 (dd, 1H, J1=7.46, J2=8.48), 8.10 (d, 1H, J=8.48), 8.16 (d, 1H, J=7.46), 8.54 (s, 1H), 13.93 (s, 1H); MS (DCI/NH3) m/z 164 [M+H]+.

Workup

  1. customThe acetic acid was removed in vacuo
  2. customleaving a pale yellow solid which
  3. filtrationfiltered through a plug of silica gel
  4. washrinsing with ethyl acetate
  5. customThe ethyl acetate was removed in vacuo
  6. customto afford a pale yellow solid

Sources & evidence

ORD record
ord-65228880b98a4bc4b94234ee5b9c2f0d
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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