Hydrochloric Acid → Ethyl 6-bromo-2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylate

HRID 649920Notes

Reaction equation

HRID 649920 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([NH:15][C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[N+:23]([O-])=O)[S:7][C:6]=2[CH:26]=1.Cl.[Sn](Cl)Cl>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([NH:15][C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[NH2:23])[S:7][C:6]=2[CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 18422148Ethyl 6-bromo-2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate

Product 1

HCID 18422173Ethyl 6-bromo-2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylateYield 40.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as in Starting Material Synthesis Example 21 and using ethyl 6-bromo-2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate (10 g), ethanol (80 ml), 18% hydrochloric acid (80 ml) and tin(II) chloride.dihydrate (20.6 g), ethyl 6-bromo-2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylate (3.8 g) was obtained.

Workup

  1. customMaterial Synthesis Example 21

Sources & evidence

ORD record
ord-b057203d5bf5430cbabe8bb712234f77
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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