Cyclopropylamine → HCID 28536514、化合物

HRID 1048984

反応式

HRID 1048984 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH:13]1([NH2:16])[CH2:15][CH2:14]1.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:13]1([NH:16][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:15][CH2:14]1

参加物

6

反応物 3

HCID 69828CyclopropylamineHCID 2926594-Iodo-3-nitroanisoleHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl

生成物 1

HCID 28536514HCID 28536514、化合物

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 1-iodo-4-methoxy-2-nitrobenzene (0.2 g, 0.0007 mol) in toluene (6.0 mL) was added cyclopropylamine (0.068 ml, 0.0008 mol) potassium tert-butoxide (0.094 g, 0.0098 mol) and Ruphos (0.049 g, 0.00010 mol) at room temperature and purged with argon for 15 min. Then Pd2(dba)3 (0.064 g, 0.00007 mol) was added and resulting mixture was heated to 100° C. in CEM microwave for 30 min. After the reaction was complete the reaction mixture was filtered through CELITE® bed and the bed was thoroughly washed with ethyl acetate. The filtrate was washed with water brine dried over Na2SO4 and concentrated under reduced pressure to afford the crude compound, which was purified by column chromatography to obtain title compound cyclopropyl-(4-methoxy-2-nitro-phenyl)-amine (yellow solid). C10H12N2O3; 1H NMR (400 MHz, CDCl3), δ: 7.98 (s, 1H), 7.60 (d, J=2.8 Hz, 1H), 7.30 (s, 1H), 7.19-7.16 (m, 1H), 4.12 (q, J=6.8, 1H), 3.80 (s, 1H), 0.89 (dd, J1=12.0 Hz, J2=6.0 Hz, 2H), 0.64 (t, J=6.8 Hz, 2H). MS (M+1): 209.1.

後処理

  1. custompurged with argon for 15 min
  2. customresulting mixture
  3. filtrationwas filtered through CELITE® bed
  4. washthe bed was thoroughly washed with ethyl acetate
  5. washThe filtrate was washed with water brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude compound, which
  9. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-8824a40aa1f342a4af373046508dcd01
出典データセット
uspto-grants-2016_07
特許番号
US09382226B2

関連ノート

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