2-Methyl-4-methoxyaniline → HCID 68157489, compound

HRID 1892675Notes

Reaction equation

HRID 1892675 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([CH3:10])[CH:4]=1.[N+:11]([C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O)([O-])=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([N:7]2[CH:16]=[C:15]3[C:14]([CH:21]=[CH:20][CH:19]=[CH:18]3)=[N:11]2)=[C:5]([CH3:10])[CH:4]=1

Participants

4

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 111012-Nitrobenzaldehyde

Product 1

HCID 68157489HCID 68157489, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methoxy-2-methylaniline (1.37 g, 10.0 mmol) and 2-nitrobenzaldehyde (1.51 g, 10.0 mmol) in tetrahydrofuran (30 mL) was stirred at reflux for 4 hours. The reaction was concentrated. To the residue was added triethyl phosphite (10 mL) and the mixture was stirred at reflux for 40 hours. The reaction was concentrated and purification by flash column chromatography gave 2-(4-methoxy-2-methylphenyl)-2H-indazole (1.5 g, 63%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 8.05 (s, 1H), 7.80 (d, J=8.8 Hz, 1H), 7.74 (d, J=8.8 Hz, 1H), 7.31-7.35 (m, 2H), 7.12-7.16 (m, 1H), 6.82-6.88 (m, 2H), 3.87 (s, 3H), 2.20 (s, 3H).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationThe reaction was concentrated
  3. additionTo the residue was added triethyl phosphite (10 mL)
  4. stirringthe mixture was stirred
  5. temperatureat reflux for 40 hours
  6. concentrationThe reaction was concentrated
  7. custompurification by flash column chromatography

Sources & evidence

ORD record
ord-64a96aeb6caa400195a2fb9ae232f5d2
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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