Hydrochloric Acid → HCID 86739574, compound

HRID 1462982Notes

Reaction equation

HRID 1462982 reaction equation
[H][H].CO.[ClH:5].[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[B:15]([OH:17])[OH:16])([O-])=[O:7]>[Pd]>[ClH:5].[OH:7][NH:6][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[B:15]([OH:17])[OH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2773548(2-Nitrophenyl)boronic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 86739574HCID 86739574, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Conditions

Temperature
24 °C

Procedure

Into a Parr shaker hydrogenation apparatus fitted with a hydrogen source and Parr bomb was charged 0.1 gm of a palladium on carbon hydrogenation catalyst obtained from Aldrich Chemical Co. under the trade designation Palladium on Carbon, 100 mL of methanol containing 1 equivalent of hydrochloric acid, and 0.8 gm of 2-nitrophenyl-boronic acid prepared in accordance with the procedure described in W. Leaman and J. R. Johnson, J. Am. Chem. Soc., 1931, 53, 711. The apparatus was sealed and was flushed with hydrogen gas and maintained under 42 psi of hydrogen at a temperature of 24° C. for 4 hr. Solids were then removed by filtration, and the filtrate was vacuum concentrated. The tan, hygroscopic solid product (mp 185°-187° C. (dec)) was isolated by filtration:

Workup

  1. customThe apparatus was sealed
  2. customwas flushed with hydrogen gas
  3. customSolids were then removed by filtration
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e8cfa36433c45d4817ddb90e36896d4
Source dataset
uspto-grants-1984_07
Patent number
US04462819

Reaction notes

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