5-Amino-2-methylphenol → HCID 9882234, compound

HRID 1609893Notes

Reaction equation

HRID 1609893 reaction equation
Cl[C:2]1[C:7]2=[CH:8][CH:9]=[CH:10][N:6]2[NH:5][C:4]([N:12]([CH3:14])[CH3:13])(N)[N:3]=1.[NH2:15][C:16]1[CH:21]=[C:20]([OH:22])[C:19]([CH3:23])=[CH:18][CH:17]=1>C(O)C>[CH3:14][N:12]([CH3:13])[C:4]1[N:3]=[C:2]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH3:23])=[C:20]([OH:22])[CH:21]=2)[C:7]2=[CH:8][CH:9]=[CH:10][N:6]2[N:5]=1

Participants

4

Reactant 2

HCID 178185-Amino-2-methylphenolHCID 21945826HCID 21945826, compound

Product 1

HCID 9882234HCID 9882234, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-chloro-2-dimethylaminopyrrolo[2,1-f][1,2,4]triazin-2-amine (50 mg, 0.26 mmol) (Tetrahedron, 3037, 52, 1996, José Ma. Quintela, María J. Moreira and Carlos Peinador) in ethanol (2.5 mL) under argon was added 5-amino-o-cresol (35 mg, 0.28 mmol). The reaction mixture was stirred overnight at 75° C. Upon cooling, a solid precipitated which was recrystallized from warm ethanol to provide 52 mg (72%) of the title compound as white solid. MS: [M+H]+=284.2, ESI [M−H]−=282.1; 1H NMR (CDCl3): δ 7.52 (s, 1H), 7.13–6.98 (m, 4H), 6.58 (s, 1H), 3.15 (s, 6H), 2.19 (s, 3H).

Workup

  1. temperatureUpon cooling
  2. customa solid precipitated which
  3. customwas recrystallized
  4. temperaturefrom warm ethanol

Sources & evidence

ORD record
ord-9cb332666cc64aa5a191acea5d4d6ec9
Source dataset
uspto-grants-2006_01
Patent number
US06982265B1

Reaction notes

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