Hydrochloric Acid → HCID 67441300, compound

HRID 1664463Notes

Reaction equation

HRID 1664463 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:18]=[CH:17][C:12]3[B:13]([OH:16])[O:14][CH2:15][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[ClH:21]>CO>[ClH:21].[NH2:1][C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:18]=[CH:17][C:12]3[B:13]([OH:16])[O:14][CH2:15][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57968891HCID 57968891, compound

Product 1

HCID 67441300HCID 67441300, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 25 mL round-bottom flask fitted with magnetic stirring bar was added 5-(4-nitro-phenoxy)-3H-benzo[c][1,2]oxaborol-1-ol (310 mg, 1.1 mmol, 1.0 eq.), followed by addition of MeOH (10 mL). The flask was evacuated and recharged with N2 twice. To the stirring solution was added 5% Pd/C (60 mg) and the flask was evacuated and recharged with H2 three times. The resulting suspension was stirred under a H2 balloon at room temperature overnight. The mixture was filtered through a short pack of celite and washed with MeOH (3×10 mL). The combined filtrate was concentrated under reduced pressure to give a light yellow oil. The oil was dissolved in minimum amount of MeOH and carefully treated with HCl (conc.). The precipitate was collected by filtration, washed with heptanes to give 5-(4-amino-phenoxy)-3H-benzo[c][1,2]oxaborol-1-ol hydrochloride salt as a white solid. LCMS (m/z) 242 (M+H); 1H NMR (DMSO-d6) δ: 9.03 (br. s., 1H), 7.64 (d, J=8.0 Hz, 1H), 6.77-6.89 (m, 4H), 6.64-6.77 (m, 2H), 4.86 (s, 2H), 3.30 (br. s., 2H).

Workup

  1. customTo a 25 mL round-bottom flask fitted with magnetic stirring bar
  2. customThe flask was evacuated
  3. additionTo the stirring solution was added 5% Pd/C (60 mg)
  4. customthe flask was evacuated
  5. filtrationThe mixture was filtered through a short pack of celite
  6. washwashed with MeOH (3×10 mL)
  7. concentrationThe combined filtrate was concentrated under reduced pressure
  8. customto give a light yellow oil
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with heptanes

Sources & evidence

ORD record
ord-11dc41016be047d88d6ec7f9b8858f12
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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