반응 #76137

반응 방정식

sodium

chloroacetonitrile

5-Amino-6-carboxyindane

→

2-Chloromethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one

용매

methanol

methanol

methanol

반응 조건

후처리

1. 1
   workup.STIRRINGAfter the reaction mixture being stirred for 1 hour at room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 1 hour at room temperature
4. 4
   workup.WAITfor a further 1 hour at 80° C. under argon
5. 5
   여과the white precipitate was collected by filtration
6. 6
   세척washed with methanol, water
7. 7
   건조dried in vacuo over P2O5 (3.15 g, 75%), mp 270-272° C.

실험 절차

Anhydrous methanol (36 ml) was added into a 250 ml round-bottomed flask that contained sodium (0.081 g) under argon. To this stirred solution chloroacetonitrile (1.56 g, 20.7 mmol) was added and stirring was continued for 30 min at room temperature under argon. 5-Amino-6-carboxyindane (European Patent Application 0602851A1; 3.19 g, 18.0 mmol) was then added and the reaction mixture was diluted with more methanol (42 ml). After the reaction mixture being stirred for 1 hour at room temperature, more anhydrous methanol (25 ml) was added and stirring was continued for 1 hour at room temperature and then for a further 1 hour at 80° C. under argon. The reaction mixture was then allowed to cool to room temperature; the white precipitate was collected by filtration, washed with methanol, water and dried in vacuo over P2O5 (3.15 g, 75%), mp 270-272° C.; 1H-NMR (DMSO-d6) 2.07 (m, 2H, 7-CH2), 2.98 (m, 4H, 6-CH2 and 8-CH2), 4.52 (s, 2H, 2-CH2), 7.50 (s, 1H, 9-H), 7.93 (s, 1H, 5-H), 12.37, (s, 1H, N3—H). MS (FAB, m/z) 235 (M+H)+;

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