Hydrochloric Acid → 4-Amino-8-bromo-N-methyl-cinnoline-3-carboxamide hydrochloric acid salt

HRID 2375586노트

반응식

HRID 2375586 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][N:9]=[C:10]([C:15]#[N:16])[C:11]([NH:13][CH3:14])=[O:12].[Cl-:17].[Al+3].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[ClH:17].[NH2:16][C:15]1[C:4]2[C:3](=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)[N:8]=[N:9][C:10]=1[C:11]([NH:13][CH3:14])=[O:12]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 866130992-[(2-bromophenyl)-hydrazono]-N-methyl-2-cyanoacetamide

생성물 1

HCID 672290504-Amino-8-bromo-N-methyl-cinnoline-3-carboxamide hydrochloric acid salt수율 90%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A 250 mL round-bottomed flask was charged with 2-[(2-bromophenyl)-hydrazono]-N-methyl-2-cyanoacetamide (2.00 g, 7.12 mmol), aluminum chloride (3.46 g, 25.97 mmol), and anhydrous toluene (68 mL). The reaction was gently refluxed for 45 minutes, cooled to room temperature, and slowly treated with 2N HCl (68 mL). A precipitate formed. The mixture was heated to 90° C. for 10minutes, cooled to room temperature, and filtered. The solids were dried under high vacuum at 50° C. to afford the title compound (2.02 g, 90%). 1H NMR (300.132 MHz, DMSO) δ 9.08 (d, J=4.7 Hz, 1H), 8.56 (dd, J=8.4, 0.8 Hz, 1H), 8.28 (dd, J=7.6, 0.7 Hz, 1H), 7.65 (t, J=8.0 Hz, 1H), 2.89 (d, J=4.7 Hz, 3H). MS APCI, m/z=281/283 (M+H). HPLC 1.61 min.

후처리

  1. temperatureThe reaction was gently refluxed for 45 minutes
  2. customA precipitate formed
  3. temperatureThe mixture was heated to 90° C. for 10minutes
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. customThe solids were dried under high vacuum at 50° C.

출처 및 근거

ORD 기록
ord-308432ce33e44e858e24338d811c7a9f
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465795B2

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