Hydrochloric Acid → HCID 86646223, compound

HRID 1257073Notes

Reaction equation

HRID 1257073 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.CCO.C1COCC1.[ClH:28]>O.[Pd]>[Cl-:28].[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:19]=[CH:18][C:15]([CH2:16][NH3+:17])=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8028TetrahydrofuranHCID 445916174-[(1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)oxy]benzonitrile

Product 1

HCID 86646223HCID 86646223, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To the solution of 4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)benzonitrile (1 g, 3.98 mmol) in a mixed solvent of EtOH (100 mL) and THF (25 mL) under N2 was added Pd/C (10 wt. %, 0.169 g). The reaction mixture was hydrogenated with a H2 balloon at room temperature with stirring for 19 h. The mixture was filtered, rotary evaporated and purified by silica gel column eluted with MeOH containing 0.6% v. NH4OH (3 mL 28-30% NH4OH to 500 mL MeOH). The white solid obtained was dissolved in water (80 mL) and 6N HCl (2 mL) was added, filtered and the filtrate was freeze-dried to give the desired salt (4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)phenyl)methanaminium chloride as white solid (0.663 g, 2.27 mmol, yield 57.1%). M.p.>230° C. 1H NMR (DMSO-d6, 300 MHz): δ 9.23 (br. s, 1H), 8.38 (br. s, 3H), 7.49 (d, J=8.4 Hz, 2H), 7.43 (d, J=8.4 Hz, 1H), 7.31 (d, J=2.4 Hz, 1H), 7.16 (dd, J=8.1 & 2.4 Hz, 1H), 7.02 (d, J=8.4 Hz, 2H), 4.97 (s, 2H) and 3.97 (q, J=5.4 Hz, 2H) ppm. Purity (HPLC): 91.1% at 220 nm and 86.1% at 254 nm. MS: m/z=256 (M+1, ESI+) and m/z=254 (M−1, ESI−).

Workup

  1. customwas hydrogenated with a H2 balloon at room temperature
  2. filtrationThe mixture was filtered
  3. customrotary evaporated
  4. custompurified by silica gel column
  5. washeluted with MeOH containing 0.6% v
  6. customThe white solid obtained
  7. filtrationfiltered
  8. customthe filtrate was freeze-dried

Sources & evidence

ORD record
ord-6920229b7b6445b0b4c9d905a7d04c04
Source dataset
uspto-grants-2013_06
Patent number
US08461336B2

Reaction notes

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