Ammonia → Ammonia
Reaction equation
[NH3:1].C(Cl)Cl.C1COCC1.Cl.[CH2:11]([NH2:14])[CH2:12][CH3:13].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[NH2:14][C:11]1[C:12]2[C:20](=[CH:19][CH:18]=[CH:17][CH:13]=2)[N:15]=[CH:16][N:1]=1.[NH3:14]Participants
Procedure
To prepare the compound I-1, a 4-hydroxy-[1,5]-naphthyridine, a 4-hydroxyquinazoline, a 5-hydroxyquinoxaline or a 4-hydroxyquinoline derivative can be converted into the corresponding chloro derivative by heating in phosphorous oxychloride between 40° C. and 100° C. neat or in an inert solvent like 1,2-DCE, or to the corresponding trifluoromethanesulphonyloxy derivative by reaction with trifluoromethanesulphonic anhydride, in the presence of an organic base between −40° C. and 80° C. in an aprotic solvent like DCM or THF (K. Ritter, Synthesis (1993), 735). The corresponding 4-amino-[1,5]-naphthyridine, 4-aminoquinazoline, 5-aminoquinoxaline or 4-aminoquinoline derivatives can then be obtained by reaction of the corresponding trifluoromethanesulphonyloxy derivatives with ammonia in a solvent like DCM or THF, or with n-propylamine hydrochloride in pyridine between −20° C. and 100° C. (R. Radinov, Synthesis (1986), 886). The corresponding 4-aminoquinazoline can also be obtained from its 4-chloro analogue by reaction with ammonia under the same conditions.
Sources & evidence
- ORD record
- ord-2fa8100dc99a4b229a35b0678e0ff847
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888359B2
Reaction notes
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