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

HRID 31093ノート

反応式

HRID 31093 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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 10 minutes, 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.

後処理

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

出典と根拠

ORDレコード
ord-2c5fed0cab084379b2887f365ccd9e4f
出典データセット
uspto-grants-2008_09
特許番号
US07425556B2

反応ノート

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