Hydrochloric Acid → 3-Amino-5-bromobenzonitrile

HRID 1527460Notes

Reaction equation

HRID 1527460 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)[C:5]#[N:6].[Sn].Cl>CO>[NH2:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([Br:1])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 51524253-Bromo-5-nitrobenzonitrileHCID 5352426Tin atom

Product 1

HCID 534069613-Amino-5-bromobenzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-5-nitrobenzonitrile (1 g, 4.4 mmol) in MeOH (50 mL) was added tin (5.23 g, 44 mmol) and 3N HCl (44 mL, 132 mmol). The reaction mixture was stirred at RT for 2 h, the filtered off and washed with MeOH. The filtrate was concentrated in vacuo, and the remaining water phase was basified to pH=12 by addition of 4N NaOH. The aqueous layer was extracted twice with EtOAc (100 mL), the combined organics were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a yellowish solid. MS (LC/MS): 197.0 [M+H]+; tR (HPLC conditions c): 4.30 min.

Workup

  1. filtrationthe filtered off
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe remaining water phase was basified to pH=12 by addition of 4N NaOH
  5. extractionThe aqueous layer was extracted twice with EtOAc (100 mL)
  6. dry with materialthe combined organics were dried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-1c457af25d144eb8ad2304df9d8284ed
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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