Chloroacetyl chloride → Trans-2-chloro-N-(1,2,3,4-tetrahydro-2-hydroxy-5-methoxy-3-naphthalinyl)-acetamide
Reaction equation
[NH2:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:12][CH3:13])[CH2:4][C@H:3]1[OH:14].C(N(CC)CC)C.[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[Cl:22][CH2:23][C:24]([NH:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:12][CH3:13])[CH2:4][C@H:3]1[OH:14])=[O:25]Participants
Procedure
1.01 g (0.005M) of trans-3-amino-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol are dissolved in 50 ml of absolute methylene chloride. 0.81 g (0.008M) of triethylamine are added, and the mixture left to cool to 0°. At this temperature, 0.68 g (0.006M) of chloroacetyl chloride (dissolved in 5 ml of absolute methylene chloride) are then added in drops over the course of 5 minutes. Stirring is effected for 2 hours at room temperature. The reaction mixture is subsequently washed once with 1N hydrochloric acid and once with ice water. It is extracted three times, each with 20 ml of methylene chloride, the combined organic phases are dried, and the solvent is concentrated by evaporation. Trans-2-chloro-N-(1,2,3,4-tetrahydro-2-hydroxy-5-methoxy-3-naphthalinyl)-acetamide is obtained (m.p. 176°-178°, recrystallisation from methylene chloride/ether).
Workup
- waitthe mixture left
- temperatureto cool to 0°
- washThe reaction mixture is subsequently washed once with 1N hydrochloric acid and once with ice water
- extractionIt is extracted three times
- dry with materialeach with 20 ml of methylene chloride, the combined organic phases are dried
- concentrationthe solvent is concentrated by evaporation
Sources & evidence
- ORD record
- ord-12fa93064c10405fa720a120bb08f0ac
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04656167
Reaction notes
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