2,3-Diaminotoluene → HCID 66901679, compound

HRID 1691440Notes

Reaction equation

HRID 1691440 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].Cl[C:11]1[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14]>C(OCCO)CCC>[CH3:1][C:2]1[C:3]2[NH:9][C:13](=[O:14])[C:12]3[CH:16]=[CH:17][C:18]([C:20]([F:23])([F:21])[F:22])=[N:19][C:11]=3[NH:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 175932,3-DiaminotolueneHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 66901679HCID 66901679, compound

Reagents, catalysts & solvents 1

HCID 81332-ButoxyethanolSolvent

Conditions

Temperature
145 °C

Procedure

A well-stirred mixture of 3-methyl-1,2-benzenediamine (4.0 g, 33 mmol) and 2-chloro-6-(trifluoromethyl)nicotinic acid (7.3 g, 33 mmol) in 2-butoxyethanol (60 ml) was heated at 140-150° C. for 6 h. The dark solution was then poured over crushed ice, and the resulting dark brown solid was collected, washed with water, and dried. Recrystallization from 50% dioxane/water afforded 7-methyl-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one.

Workup

  1. additionThe dark solution was then poured
  2. customover crushed ice
  3. customthe resulting dark brown solid was collected
  4. washwashed with water
  5. customdried
  6. customRecrystallization from 50% dioxane/water

Sources & evidence

ORD record
ord-ce5f546d8c7c49c7bdbf99f81ffafa50
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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