Hydrochloric Acid → 5-Amino-2,1-benzoxaborol-1(3H)-ol

HRID 1425932

반응식

HRID 1425932 반응식
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[B:8]([OH:11])[O:9][CH2:10][C:6]=2[CH:5]=1)([O-])=O.Cl>CO.[Zn]>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]2[B:8]([OH:11])[O:9][CH2:10][C:6]=2[CH:5]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 68281436HCID 68281436, 화합물

생성물 1

HCID 597551995-Amino-2,1-benzoxaborol-1(3H)-ol수율 83%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

To a solution of 5-nitrobenzo[c][1,2]oxaborol-1(3H)-ol (CII) (360 mg, 2.01 mmol) in MeOH (25 mL) was added Zn dust (1.31 g, 20.11 mmol) and 2 M HCl (30 mL, 60.33 mmol). The reaction mixture was stirred at room temperature for 2.5 h before saturating with 5% aq. NaHCO3 (40 mL). The solids were filtered and filtrate was concentrated under reduce pressure to about 50 mL. The residue was diluted with EtOAc and the phases were separated. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give 5-aminobenzo[c][1,2]oxaborol-1(3H)-ol (CIII) as a brown oil (250 mg, 1.68 mmol, 83% yield, 80% purity). ESIMS found for C7H8BNO2 m/z 149.9 (M+H). The crude product was used without further purification for coupling.

후처리

  1. concentrationbefore saturating with 5% aq. NaHCO3 (40 mL)
  2. filtrationThe solids were filtered
  3. concentrationfiltrate was concentrated
  4. additionThe residue was diluted with EtOAc
  5. customthe phases were separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ca8b7b2d4036495fbfda4a54d40dd04a
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933018B2

연결된 노트

불러오는 중…