O-Toluidine → HCID 10332347, compound

HRID 973564Notes

Reaction equation

HRID 973564 reaction equation
[NH2:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][C:14]1[C:15]([CH3:20])=[CH:16][CH:17]=[CH:18][CH:19]=1>C(O)C>[NH2:1][C:2]1[N:11]=[C:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 104422884-chloroquinazolin-2-amine

Product 1

HCID 10332347HCID 10332347, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-4-chloroquinazoline (0.64 g, 0.0036 mol) was heated to 170° in o-toluidine (1 ml, 0.008 mol) for 1 hour. The reaction mixture was dissolved in ethanol, stripped and partitioned between chloroform and NaOH solution (pH 9). The organic solution was dried, filtered and excess solvent removed to give an oil which afforded crystals of 2-amino-4-(2-methylphenylamino)-quinazoline (0.55 g, 62%) m.p. 273°-275° (from ethanol).

Workup

  1. custompartitioned between chloroform and NaOH solution (pH 9)
  2. customThe organic solution was dried
  3. filtrationfiltered
  4. customexcess solvent removed
  5. customto give an oil which

Sources & evidence

ORD record
ord-fe260666ec40421e802a18037708db9a
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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