2-Methyl-2-butanol → 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzamide
Reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:6][C:3]=1[C:4]#[N:5].C([OH:27])(CC)(C)C>C(Cl)Cl>[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[CH:6][C:3]=1[C:4]([NH2:5])=[O:27]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 79 °C
Procedure
After repetition of the reduction step, a methylene chloride solution (894.3 kg) containing 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile (81.6 kg) was added portionwise to tert-amyl alcohol (186 kg) and the resultant mixture was distilled until the temperature of the distillate reached 57° C. Additional tert-amyl alcohol (726 kg) was added portionwise and distillation was continued until the residual volume of the reaction mixture was approximately 770 liters. Potassium hydroxide (flaked form; 51 kg) was added and the mixture was heated to 79° C. for 4 hours. The resultant mixture was cooled to ambient temperature to provide a solution of 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzamide which was used without being isolated.
Workup
- distillationthe resultant mixture was distilled until the temperature of the distillate
- customreached 57° C
- additionAdditional tert-amyl alcohol (726 kg) was added portionwise
- distillationdistillation
- additionPotassium hydroxide (flaked form; 51 kg) was added
- temperatureThe resultant mixture was cooled to ambient temperature
Sources & evidence
- ORD record
- ord-922d6e2e4fb5489c9676dcc6d8e4e890
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705145B2
Reaction notes
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