Methyl 3-amino-4-propylbenzoate → HCID 178438014, compound

HRID 1699900Notes

Reaction equation

HRID 1699900 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][CH3:14])[C:5]([O:7][CH3:8])=[O:6].[N:15]([O-])=O.[Na+]>C(O)(=O)C.O>[CH2:13]([C:12]1[C:11]2[C:2](=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=2)[NH:1][N:15]=1)[CH3:14]

Participants

5

Reactant 2

HCID 22387873Methyl 3-amino-4-propylbenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 178438014HCID 178438014, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-amino-4-propylbenzoate (5.07 g) in acetic acid (150 ml) was dropwise added a solution of sodium nitrite (2.07 g) in water (5 ml) for 5 min. After stirring for 20 min, the reaction mixture was concentrated, and then toluene and a saturated aqueous sodium hydrogencarbonate solution were added to the residue. The separated toluene layer was dried over sodium sulfate and concentrated. The residue was allowed to stand and partially solidified. The solid was washed with hexane and dried to give the object compound (2.44 g) as a brown solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiontoluene and a saturated aqueous sodium hydrogencarbonate solution were added to the residue
  3. dry with materialThe separated toluene layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. washThe solid was washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-943b932b36f3488296b1eb696e414c58
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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