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

HRID 1520836Notes

Reaction equation

HRID 1520836 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-a42b192d4e3f49869b2567e05fd86709
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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