Ammonia → 3-Amino-4-methoxybenzo[b]thiophene-2-carboxamide

HRID 2226870Notes

Reaction equation

HRID 2226870 reaction equation
[NH2-:1].[Li+].N.[Li].[NH2:5][C:6]1[C:7]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:8]=2[S:9][C:10]=1[C:11](OC)=[O:12]>O1CCCC1>[NH2:5][C:6]1[C:7]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:8]=2[S:9][C:10]=1[C:11]([NH2:1])=[O:12]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 24532Lithium amideHCID 3028194LithiumHCID 10799875Methyl 3-amino-4-methoxy-1-benzothiophene-2-carboxylate

Product 1

HCID 189637773-Amino-4-methoxybenzo[b]thiophene-2-carboxamideYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium amide in liquid ammonia is prepared as described by Unangst P. C., Carethers M. E., J. Heterocyclic. Chem. 21, 709 (1984), from lithium metal ribbon (0.16 g, 23 mmol). A solution of methyl 3-amino-4-methoxybenzo[b]thiophene-2-carboxylate (1.3 g, 5.5 mmol) [Beck J. R., supra] in 10 mL of tetrahydrofuran is added dropwise. The mixture is stirred for 18 hours as the excess ammonia is permitted to evaporate. The residue is treated with 250 g of ice and water. The solid product is filtered, washed with water, and recrystallized from aqueous ethanol to yield 0.70 g (58%) of product; mp=151°-153° C.

Workup

  1. customto evaporate
  2. additionThe residue is treated with 250 g of ice and water
  3. filtrationThe solid product is filtered
  4. washwashed with water
  5. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-cc7faf2a6f574025a0556557bec87510
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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