Stannous chloride dihydrate → (3-Amino-4-benzyloxy-phenoxy)-acetonitrile

HRID 1106733Notes

Reaction equation

HRID 1106733 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([O:13][CH2:14][C:15]#[N:16])=[CH:11][C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:19][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[O:13][CH2:14][C:15]#[N:16]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 18789746(4-Benzyloxy-3-nitro-phenoxy)-acetonitrile

Product 1

HCID 18789661(3-Amino-4-benzyloxy-phenoxy)-acetonitrileYield 97.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 6.9 g (4-benzyloxy-3-nitro-phenoxy)-acetonitrile, 200 ml of ethyl acetate, and 27.4 g of tin (II) chloride dihydrate was stirred at room temperature for 17 hours, poured into ethyl acetate, added saturated sodium bicarbonate solution, extracted twice with ethyl acetate, dried (MgSO4), evaporated, and obtained 6.0 g of (3-amino-4-benzyloxy-phenoxy)-acetonitrile as a light brown oil.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-bfb7e620fa344867a7962b3cf6d343a2
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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