O-Phenylenediamine → N-(2-aminophenyl)-6-chloronicotinamide

HRID 1695028ノート

反応式

HRID 1695028 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.Cl.C(N=C=NCCCN(C)C)C.O[C:24]1[C:32]2[N:31]=N[NH:29][C:28]=2[CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[NH2:29][C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][C:32]=1[NH:31][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1

参加物

8

反応物 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 22478760N-(2-aminophenyl)-6-chloronicotinamide収率 56%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

6-Chloronicotinic acid (157.5 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and o-phenylenediamine (216 mg, 2 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine and extracted with 200 ml of ethyl acetate. The ethyl acetate was removed under vacuum. To the residue was added 5 ml of absolute ethanol. The solids were collected by vacuum filtration, washed with absolute ethanol and dried under vacuum to give the title compound (138 mg, 56% yield) as a brown solid. LC-MS (m/z) 248 (M+1).

後処理

  1. additionwere added
  2. extractionextracted with 200 ml of ethyl acetate
  3. customThe ethyl acetate was removed under vacuum
  4. additionTo the residue was added 5 ml of absolute ethanol
  5. filtrationThe solids were collected by vacuum filtration
  6. washwashed with absolute ethanol
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-2962c4562a6a4c9685150a501a0ac802
出典データセット
uspto-grants-2012_04
特許番号
US08158656B2

反応ノート

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