Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[C:15]1([C:20](O)=O)[CH2:19][CH2:18][CH2:17][CH:16]=1>>[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]3[NH:11][C:20]([C:15]4[CH2:19][CH2:18][CH2:17][CH:16]=4)=[N:1][C:2]=3[CH:3]=2)[NH:7][C:6]1=[O:12]Participants
Procedure
Analogously to Example 11, a mixture of 0.48 g. 5,6-diamino-3,3-dimethylindolin-2-one and 0.31 g. (1-cyclopenten-1-yl)-carboxylic acid is well stirred up with 4.5 g. warm polyphosphoric acid and then stirred for 30 minutes in a bath with a temperature of 200° C. After cooling, the reaction mixture is triturated with ice water, adjusted to pH 7-8 with concentrated aqueous ammonia solution and insoluble material is filtered off with suction, washed with water and dried, 0.51 g. of crude product thereby being obtained. This is repeatedly triturated with 6 ml. amounts of methanol, 0.25 g. of substance thereby remaining undissolved. This product is triturated three times with 6 ml. amounts of a mixture of methylene chloride/methanol (1:1 v/v), 0.14 g. of the desired title compound thereby being obtained which, per mole, still contains 2/3 mole methanol and 1 mole water; m.p. 233°-235° C.
Workup
- additionAnalogously to Example 11, a mixture of 0.48 g
- temperatureAfter cooling
- customthe reaction mixture is triturated with ice water
- filtrationis filtered off with suction
- washwashed with water
- customdried
- customof crude product thereby being obtained
- customThis is repeatedly triturated with 6 ml
- customThis product is triturated three times with 6 ml
- additionamounts of a mixture of methylene chloride/methanol (1:1 v/v), 0.14 g
Sources & evidence
- ORD record
- ord-263c974627b54a3ca252358991ab89cd
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04730003
Linked notes
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