Stannous chloride dihydrate → 7-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

HRID 659316Notes

Reaction equation

HRID 659316 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][C:10]([I:16])=[CH:9][N:8]=1)C.O.O.Cl[Sn]Cl>C(O)C>[I:16][C:10]1[CH:9]=[N:8][C:7]2[NH:6][CH2:5][C:4](=[O:3])[NH:13][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 57885827Ethyl (5-Iodo-3-nitropyridin-2-yl)glycinate

Product 1

HCID 448291147-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(5-Iodo-3-nitro-pyridin-2-ylamino)-acetic acid ethyl ester (17 g) was dissolved in ethanol. SnCl2.2H2O was added and the reaction mixture was heated to 80° C. for two (2) hours. The resulting precipitate was filtered and washed with ethanol to give the title compound as a rust colored solid (59-77% yield). M.p. 81° C., LCMS: m/z=275.91 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 3.94 (s, 2H), 6.94 (bs, 1H), 7.12 (d, J=1.8 Hz, 1H), 7.74 (s, J=1.8 Hz, 1H), 10.40 (bs, 1H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-ac4913b3e5ce4fc59e72a94ee173878a
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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