Water → 6-bromo-1,2,3,4-tetrahydro-2,2-dimethyl-4-Quinolinamine

HRID 20037ノート

反応式

HRID 20037 の反応式
[N:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[NH:7][C:6]([CH3:16])([CH3:15])[CH2:5]1)=[N+]=[N-].O.C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(C)=O>[Br:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:15])([CH3:16])[CH2:5][CH:4]2[NH2:1]

参加物

6

反応物 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 866141294-Azido-6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 673058276-bromo-1,2,3,4-tetrahydro-2,2-dimethyl-4-Quinolinamine

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-azido-6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (2.29 g, 8.15 mmol), water (6.50 ml, 361 mmol), and THF (20.4 ml, 8.15 mmol) was added triphenylphosphine (2.35 g, 8.96 mmol) in one portion. The resulting mixture was heated to 40 deg C. and stirred overnight. The crude mixture was dissolved with EtOAc and transferred to a sep. funnel containing 0.5 MHCl. The aqueous layer was washed 5×DCM. The aqueous layer was then neutralized with 6N NaOH and washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to provide the desired product. MS m/z: 239 (M−NH2).

後処理

  1. temperatureThe resulting mixture was heated to 40 deg C
  2. additionfunnel containing 0.5 MHCl
  3. washThe aqueous layer was washed 5×DCM
  4. washwashed 3× with EtOAc
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2409dcfe163049e4b8ef9642f3d75801
出典データセット
uspto-grants-2010_06
特許番号
US07745484B2

反応ノート

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