Hydrochloric Acid → 6-(2-aminoethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride

HRID 1037037Notes

Reaction equation

HRID 1037037 reaction equation
[CH3:1][C:2]1([CH3:17])[O:6][B:5]([OH:7])[C:4]2[CH:8]=[C:9](/[CH:12]=[CH:13]/[N+:14]([O-])=O)[CH:10]=[CH:11][C:3]1=2.[ClH:18]>CO.[OH-].[OH-].[Pd+2]>[ClH:18].[NH2:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:3]2[C:2]([CH3:1])([CH3:17])[O:6][B:5]([OH:7])[C:4]=2[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86685484(E)-3,3-dimethyl-6-(2-nitrovinyl)benzo[c][1,2]oxaborol-1(3H)-ol

Product 1

HCID 866854826-(2-aminoethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of (E)-3,3-dimethyl-6-(2-nitrovinyl)benzo[c][1,2]oxaborol-1(3H)-ol (117 mg, 0.5 mmol) in MeOH (15 mL) at rt was added Pd(OH)2 (20%) dust (48 mg, 0.078 mmol) and HCl (3N, 0.3 mL). The reaction mixture was stirred at rt for 8 h under H2 atmosphere. Methanol was added and the mixture was filtered through Celite. The organic layer was concentrated under reduced pressure to give the crude compound 6-(2-aminoethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride as a light yellow oil. It was used in next step without further purification. MS: m/z=206.1 (M+1, ESI+).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-512b50dc05dc4a01ab435b84c4b2c149
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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