Water → HCID 21277190, compound

HRID 2292353Notes

Reaction equation

HRID 2292353 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10]C)[C:7]([O:12]C)=[CH:6][C:3]=1[C:4]#[N:5].B(Br)(Br)Br.O>ClCCl>[NH2:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([OH:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 7359672-Amino-4,5-dimethoxybenzonitrile

Product 1

HCID 21277190HCID 21277190, compoundYield 142.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 15.65 g (87.83 mmol) of 2-amino-4,5-dimethoxybenzonitrile in 440 ml of dry dichloromethane was added dropwise at -78° C., 66.0 g (263.5 mmol) of boron tribromide. The mixture was stirred overnight while the mixture was allowed to warm to room temperature. After the addition of 180 ml of water, the resulting precipitate was filtered off and dried in vacuo (37.6 g). The crude material was dissolved in 570 ml of methanol, 0.5 ml of concentrated hydrochloric acid was added and the mixture was refluxed for 1 hour. Evaporation to dryness yielded 18.75 g of 2-amino-4,5-dihydroxybenzonitrile as the hydrobromide salt.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. customdried in vacuo (37.6 g)
  3. dissolutionThe crude material was dissolved in 570 ml of methanol
  4. addition0.5 ml of concentrated hydrochloric acid was added
  5. temperaturethe mixture was refluxed for 1 hour
  6. customEvaporation to dryness

Sources & evidence

ORD record
ord-492f561f44ed4d0292abc5a8e54119b1
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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