Hydrochloric Acid → 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile

HRID 646534Notes

Reaction equation

HRID 646534 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:9][O:10][C:11]1[C:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:17][C:14]([C:15]#[N:16])=[C:13]([N+:29]([O-])=O)[CH:12]=1.Cl.[OH-].[Na+]>O>[NH2:29][C:13]1[CH:12]=[C:11]([O:10][CH3:9])[C:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[CH:17][C:14]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 117235824-Methoxy-5-[3-(4-morpholinyl)propoxy]-2-nitrobenzonitrile

Product 1

HCID 100628722-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrileYield 104.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Sodium dithionite (89%, 81.4 kg) was added to a stirred slurry of 4-methoxy-5-(3-morpholinopropoxy)-2-nitrobenzonitrile (48.8 kg) in water (867 liters) and the resultant mixture was heated to 50° C. for approximately 2 hours to complete the reaction. The temperature of the reaction mixture was raised to approximately 70° C. and a concentrated aqueous hydrochloric acid solution (36%, 270 kg) was added over 3 hours. The resultant mixture was cooled to 20-25° C. and sodium hydroxide liquor (47%, 303.7 kg) was added whilst stirring of the reaction mixture was continued. The reaction mixture was extracted with two portions of methylene chloride (1082 kg and 541 kg respectively) and the combined organic extracts were washed with water (510 liters). The organic phase was concentrated by distillation to remove 800 liters of solvent. There was thus obtained a methylene chloride solution (503.5 kg) containing 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile (46.3 kg, 99% yield) suitable for use in the next stage.

Workup

  1. customthe reaction
  2. extractionThe reaction mixture was extracted with two portions of methylene chloride (1082 kg and 541 kg respectively) and the combined organic extracts
  3. washwere washed with water (510 liters)
  4. concentrationThe organic phase was concentrated by distillation
  5. customto remove 800 liters of solvent
  6. customThere was thus obtained a methylene chloride solution (503.5 kg)

Sources & evidence

ORD record
ord-8373b21c2987438cbabb5a386aefc8d9
Source dataset
uspto-grants-2010_04
Patent number
US07705145B2

Reaction notes

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