Chlorosuccinimide → 3-Chloro-1,2-diamino-5-methoxybenzene

HRID 70947Notes

Reaction equation

HRID 70947 reaction equation
[Cl:1][C:2]1[C:7]2[NH:8][N:9]=[N:10][C:6]=2[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1.[Cl:13][C:14]1[C:15]([NH2:23])=[C:16]([NH2:22])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1.[CH3:24][O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=1.[Cl:36]N1C(=O)CCC1=O>>[NH2:22][C:16]([CH3:24])([CH2:17][N:9]1[N:10]=[C:6]2[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=[C:2]([Cl:1])[C:7]2=[N:8]1)[C:15]#[N:23].[Cl:1][C:2]1[C:7]2[NH:8][N:9]=[N:10][C:6]=2[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1.[Cl:13][C:14]1[C:15]([NH2:23])=[C:16]([NH2:22])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1.[Cl:36][C:31]1[C:29]([NH2:30])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=[C:26]([O:25][CH3:24])[CH:32]=1

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 667934-Methoxy-2-nitroanilineHCID 234534193-Chloro-1,2-diamino-5-methoxybenzeneHCID 178491885HCID 178491885, compound

Product 4

HCID 151122632-Chloro-4-methoxy-6-nitroanilineYield 14%HCID 234534193-Chloro-1,2-diamino-5-methoxybenzeneYield 75%HCID 666206832-amino-3-(4-chloro-6-methoxy-2H-benzotriazol-2-yl)-2-methylpropionitrileHCID 178491885HCID 178491885, compound

Procedure

2-amino-3-(4-chloro-6-methoxy-2H-benzotriazol-2-yl)-2-methylpropionitrile was prepared using a procedure similar to that described in Example 1, part a and b, except starting from 7-chloro-5-methoxy-1H-benzotriazole. 7-Chloro-5-methoxy-1H-benzotriazole (0.8 g) was prepared using a procedure similar to that described in Example 13, part a, except starting from 3-chloro-1,2-diamino-5-methoxybenzene. 3-Chloro-1,2-diamino-5-methoxybenzene (1.88 g, 75%) was prepared using a procedure similar to that described in Example 38, part a and b, except starting from 4-methoxy-2-nitroaniline (16.8 g) and N-chlorosuccinimide (15 g) in part a to yield 6-chloro-4-methoxy-2-nitroaniline (2.9 g, 14%) used in part b.

Sources & evidence

ORD record
ord-4cea1ea065c24c4dac498bff327fc687
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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