Ammonia → HCID 66592603, compound

HRID 1389134Notes

Reaction equation

HRID 1389134 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH3:12][O:13][C:14]1[C:19]2[O:20][C:21]([CH2:23][CH2:24]O)=[CH:22][C:18]=2[CH:17]=[CH:16][CH:15]=1.[NH3:26]>O1CCCC1>[CH3:12][O:13][C:14]1[C:19]2[O:20][C:21]([CH2:23][CH2:24][NH2:26])=[CH:22][C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 85570p-ToluenesulfonateHCID 70559414HCID 70559414, compound

Product 1

HCID 66592603HCID 66592603, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 26.7 g of the tosylate of 7-methoxy-3-benzofuranethanol (Example 2a), prepared as described in Example 1b, 300 ml of tetrahydrofuran and 100 g of ammonia was heated in a pressure vessel to 100° for 4 hours. The crude product was partitioned into basic and neutral fractions, and the basic fraction short-path distilled (to 170° bath temperature, 1 micron pressure) to give 11.2 g (76%) of 7-methoxy-3-benzofuranethylamine; nmr spectrum (in CDCl3): τ2.6 (s, 1); 2.9-3.4 (m, 3); 6.1 (s, 3); 6.9-7.5 (m, 4) and 8.9 (s, 2).

Workup

  1. customprepared
  2. temperaturewas heated in a pressure vessel to 100° for 4 hours
  3. customThe crude product was partitioned into basic and neutral fractions
  4. distillationthe basic fraction short-path distilled (to 170° bath temperature, 1 micron pressure)

Sources & evidence

ORD record
ord-c7e421ea7b714869a75dec2b263a80df
Source dataset
uspto-grants-1981_01
Patent number
US04243668

Reaction notes

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