Water → 7-Methoxy-1-naphthaleneethanamine

HRID 1099497Notes

Reaction equation

HRID 1099497 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C:13](=O)[C:14]([NH2:16])=O)=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].B.C1COCC1.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH2:16])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 6451240Aluminum(III) ChlorideHCID 446285742-(7-Methoxy-1-naphthyl)-2-oxoacetamide

Product 1

HCID 110526677-Methoxy-1-naphthaleneethanamineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

480 mg of the compound obtained in Step B dissolved in THF (20 ml) are introduced into a reactor, followed by 2 eq. of AlCl3 and finally, slowly, 6 eq. of BH3.THF solution, and the reaction mixture is stirred for 2.5 hours. Water (12 ml) is then added, followed by 25 ml of 1N sodium hydroxide solution together with 800 mg of solid sodium hydroxide, and three extractions with methyl tert-butyl ether (20 ml) are carried out. The solvents are then dried over Na2SO4 and then evaporated off to yield the title product in the form of a yellow oil in a yield of 80% and with a chemical purity of 95%.

Workup

  1. additionare introduced into a reactor
  2. extractionfollowed by 25 ml of 1N sodium hydroxide solution together with 800 mg of solid sodium hydroxide, and three extractions with methyl tert-butyl ether (20 ml)
  3. dry with materialThe solvents are then dried over Na2SO4
  4. customevaporated off

Sources & evidence

ORD record
ord-41660d18846943c58717262e5b95c6bb
Source dataset
uspto-grants-2012_03
Patent number
US08143449B2

Reaction notes

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