HCID 178418361, compound → HCID 178507384, compound

HRID 1666104Notes

Reaction equation

HRID 1666104 reaction equation
[C@H:1]1([NH:10][C:11]2[O:12][CH2:13][C:14]3[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H][H]>O1CCCC1.[Ni]>[C@H:1]1([NH:10][C:11]2[O:12][CH2:13][C:14]3[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178526510HCID 178526510, compound

Product 1

HCID 178507384HCID 178507384, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-indan-1-yl-(5-nitro-4H-benzo[d][1,3]oxazin-2-yl)-amine (example 1) (1.90 g, 6.1 mmol) in tetrahydrofuran (250 mL) at 23° C. were added three Pasteur pipettes of Raney-Nickel (ready to use 10% suspension in water) and the mixture was vigourously stirred under an atmospheric pressure of hydrogen for 23 h. The catalyst was filtered off, washed with tetrahydrofuran, the solvent was removed in vacuum to give the title compound as a light yellow foam (1.81 g, 99%), MS (ISP) m/e=280.4 [(M+H)+].

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with tetrahydrofuran
  3. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-6bf61f58fe674d09b67d0922e0eb098c
Source dataset
uspto-grants-2011_10
Patent number
US08044047B2

Reaction notes

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