Ammonia → 2-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester

HRID 1941951Notes

Reaction equation

HRID 1941951 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[C:6]([N+:16]([O-])=O)[C:5]=1[S:19][C:20]#[N:21].N>C(O)(=O)C.O.[Fe]>[CH3:1][O:2][C:3]([C:4]1[C:5]2[S:19][C:20]([NH2:21])=[N:16][C:6]=2[CH:7]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:9]=1)=[O:22]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 57813637HCID 57813637, compound

Product 1

HCID 578136562-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl esterYield 46.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3-Nitro-5-pyridin-3-yl-2-thiocyanato-benzoic acid methyl ester (1.1 g, 3.49 mmol) in glacial acetic acid (23 ml) was treated with iron powder (0.97 g, 17.5 mmol) and stirred at ambient temperature for 16 h. The resultant mixture was diluted with water (200 ml) and made alkaline by the addition of concentrated ammonia solution. The mixture was filtered and the filtrate extracted with ethyl acetate (3×200 ml). The filtered solid was extracted with boiling ethanol (3×250 ml) and the combined organic fractions evaporated to dryness to give 2-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester as an off-white solid (0.46 g, 46%).

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate extracted with ethyl acetate (3×200 ml)
  3. extractionThe filtered solid was extracted with boiling ethanol (3×250 ml)
  4. customthe combined organic fractions evaporated to dryness

Sources & evidence

ORD record
ord-96f5f535292e41539a0be8952370d592
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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