Water → (3-Aminonaphthalen-2-yl)methanol

HRID 604619노트

반응식

HRID 604619 반응식
[NH2:1][C:2]1[C:3]([C:12](O)=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[C:3]([CH2:12][OH:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 222443-Amino-2-naphthoic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 10374898(3-Aminonaphthalen-2-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 3-amino-2-naphthoic acid (85%, 1.17 g, 5.34 mmol) in dry THF (20 mL) was added dropwise over 30 min to a stirred solution of lithium aluminum hydride (95%, 0.53 g, 13.4 mmol) in dry THF (20 mL) at 0° C. under N2. The mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was adjusted to basic pH with 1N NaOH (20 mL). The mixture was filtered and extracted with Et2O (4×100 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-amino-2-naphthyl)methanol. LCMS calc.=174.1; found=174.2 (M+1)+. 1H NMR (500 MHz, CD3OD): δ 7.66 (d, J=8.0 Hz, 1H); 7.61 (s, 1H); 7.55 (d, J=8.2 Hz, 1H); 7.30-7.27 (m, 1H); 7.18-7.14 (m, 1H); 7.08 (s, 1H); 4.74 (s, 2H).

후처리

  1. filtrationThe mixture was filtered
  2. extractionextracted with Et2O (4×100 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-348fc64e6adf44ebbb9a5667e018867c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

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