HCID 59464154, compound → HCID 59464341, compound

HRID 1713892Notes

Reaction equation

HRID 1713892 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([C:9]2[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][CH:10]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]>C(OCC)(=O)C.[Pt]=O>[Cl:1][C:2]1[CH:8]=[C:7]([CH:9]2[CH2:10][CH2:11][C:12]3([O:13][CH2:14][CH2:15][O:16]3)[CH2:17][CH2:18]2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

4

Reactant 1

HCID 59464154HCID 59464154, compound

Product 1

HCID 59464341HCID 59464341, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

Platinum oxide (200 mg) was added in one portion to a stirred solution of 2-chloro-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)aniline (3.8 g, 14.3 mmol) in ethyl acetate (50 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 8 h. The reaction mixture was filtered and concentrated in vacuo to leave the title compound (2.4 g, 63%) as a solid; 1H NMR δ 1.5-1.65 (4H, m), 1.67-1.8 (4H, m), 2.38-2.48 (1H, m), 3.88 (4H, s), 5.1 (2H, s), 6.72 (1H, d), 6.9 (1H, dd), 7.0 (1H, d); MS m/e MH+ 268.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fcbed19dad754d57a7651e42def6b1fa
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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