[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13]#[N:14])(=[O:3])[CH3:2].[OH2:15].C([O-])([O-])=O.[Na+].[Na+].[NH2:22]O.Cl>C(O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13](=[N:22][OH:15])[NH2:14])(=[O:3])[CH3:2]1-acetyl-2,3-dihydro-1H-indole-2-carbonitrile (0.0132 mole) was treated with water (54 ml) and the resulting suspension was treated sequentially with Na2CO3 (0.00726 mole) and NH2OH.HCl 0.0145 mole). The mixture was treated with ethanol (26 ml) and heated to 80–90° C. Upon achieving reaction temperature, the mixture was still a suspension. Added another 26 ml of ethanol which afforded a clear solution. The reaction was heated for 2.5 hours and cooled to room temperature with stirring. A voluminous precipitate formed which was collected by suction filtration, washed with cold distilled water, and air dried, yielding 2.23 g of 1-acetyl-2,3-dihydro-N′-hydroxy-1H-indole-2-carboximidamide (intermediate 14, mp. 204–205° C.).
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