Hydrochloric Acid → 929022-07-1

HRID 606632

반응식

HRID 606632 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:5]=1N.Cl.N([O-])=O.[Na+].[Cu][C:20]#[N:21]>O.C(Cl)(Cl)Cl>[C:20]([C:5]1[C:6]([O:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:13])#[N:21]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 602320Methyl 2-amino-3-methoxybenzoate2회HCID 23668193Sodium NitriteHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 58854057929022-07-1

시약·촉매·용매 2

HCID 962Water용매3회HCID 6212Chloroform용매

실험 절차

A suspension of methyl-2-amino-3-methoxybenzoate (Intermediate 36, 2.27 g, 12.5 mmol) in water (10 mL) and con. HCl (2 mL) was cooled to 0 deg. C. and a solution of sodium nitrite (1.04 g, 15 mmol) in water (10 mL) was added dropwise. The resulting solution was stirred cold for 30 min. then added to a suspension of copper(I)cyanide (3.4 g, 38 mmol) in water (100 mL). The resulting suspension was heated at 60 deg. C. for 3 h, cooled, chloroform was added and the mixture was filtered through celite. The organic layer was dried (MgSO4), the solvent was evaporated and the residue was flash chromatographed eluting with 0-50% hexane-ethyl acetate affording Intermediate 37 (0.56 g, 23.5%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.99 (s, 6 H), 7.20 (d, J=8.35 Hz, 1 H), 7.61 (t, J=8.13 Hz, 1 H), 7.68 (d, J=7.47 Hz, 1 H).

후처리

  1. temperatureThe resulting suspension was heated at 60 deg. C
  2. waitfor 3 h
  3. temperaturecooled
  4. filtrationthe mixture was filtered through celite
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent was evaporated
  7. customchromatographed
  8. washeluting with 0-50% hexane-ethyl acetate affording Intermediate 37 (0.56 g, 23.5%) as a yellow solid

출처 및 근거

ORD 기록
ord-d7e35c0b6860420ab3f56a905ffa6df1
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915410B2

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