Methyl Salicylate → HCID 14625931, compound
Reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[H-].[Na+].[Na].[NH:22]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=[O:29]>C1(C)C=CC=CC=1>[CH3:11][O:10][C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:22]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=[O:29])=[O:9]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
3.04 g of methyl salicylate and 18.4 g of 1,5-dibromopentane were added to a solution of 1.06 g of 50% sodium hydride in toluene, heated to 100° C. for 3 hurs, washed with water, dried, freed from the solvent by distillation off at reduced pressure and then further distilled to obtain an oily substance. A mixture of the thus obtained oily substance and 2.70 g of sodium salt of azacycloheptane-2-one was heated to 100° C. in toluene solvent for 5 hours, washed with water, dried and freed from the solvent by distillation off at reduced pressure and then finally distilled to obtain 4.90 g of colorless 1-[5-(2-methoxycarbonylphenoxy) pentyl] azacycloheptane-2-one having the following appearance, column temperature and analysis:
Workup
- washwashed with water
- customdried
- distillationfreed from the solvent by distillation off at reduced pressure
- distillationfurther distilled
- customto obtain an oily substance
- washwashed with water
- customdried
- distillationfreed from the solvent by distillation off at reduced pressure
- distillationfinally distilled
Sources & evidence
- ORD record
- ord-f5947f30ac5342328fab86ad627306e3
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04882359
Reaction notes
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