Stannous Chloride → 5,6-Dichloropyridine-2,3-diamine

HRID 343774

반응식

HRID 343774 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1.[Cl:12][Sn]Cl>Cl>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:11])=[C:4]([Cl:12])[N:3]=1

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 2241682-Amino-5-chloro-3-nitropyridine

생성물 1

HCID 134926415,6-Dichloropyridine-2,3-diamine

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

The compounds of the present invention may be prepared as follows. It has been reported that reduction of 2-amino-5-chloro-3-nitropyridine (2) by SnCl2 in concentrated HCl resulted in both reduction of the nitro group to an amino group as well as chlorination of the pyridine ring to give 2,3-diamino-5,6-dichloropyridine (4) as the only isolated product (Israel & Day, J. Org. Chem. 24:1455-1460 (1959)). We found that reduction of 2 under identical conditions as reported gave a mixture of 2,3-diamino-5-chloropyridine (3) and 2,3-diamino-5,6-dichloropyridine (4) in a ratio of 4:1. The mixture could not be separated by crystallization in water. It could be separated by preparative TLC and chromatography. Cyclization of 3 with oxalic acid gave 8-NQX 5 and cyclization of 4 with oxalic acid gave 8-NQX 6. 6,7-dichloro-8-NQX 6 was found to have a Ki of about 200 nM, which is similar to the corresponding 6,7-dichloro-QX. 6-Chloro-8-NQX 5 also was found to be about as active as the corresponding 6-chloro-QX. 6-Bromo-7-methyl-8-NQX (8) was found to have a Ki of about 200 nM. 6-NQX 11 and 6,8-diN-QX 13 also were found to be about as active as QX. ##STR8##

후처리

  1. customThe compounds of the present invention may be prepared
  2. customresulted in both reduction of the nitro group to an amino group as well as chlorination of the pyridine ring

출처 및 근거

ORD 기록
ord-b4570dbcf2864769b14fd572c8f7e79e
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05863916

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