Sodium hydride → HCID 136342113, compound

HRID 748521Notes

Reaction equation

HRID 748521 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([O-:3])=[O:2].[H-].[Na+].[CH2:16]([O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23](Cl)=[N:22][CH:21]=1)[CH3:17]>C[N-]C.O.[NH4+].[Cl-]>[OH:13][C:8]1[NH:9][C:10]2[C:6]([C:7]=1[C:23]1[CH:24]=[CH:25][C:20]([C:19]([O:18][CH2:16][CH3:17])=[O:27])=[CH:21][N:22]=1)=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 2303665-Nitro-2-oxindoleHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 136342113HCID 136342113, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 25517Ammonium ChlorideSolventHCID 182180DimethylazanideSolvent

Conditions

Temperature
135 °C

Procedure

To a cooled solution of 5-nitrooxindol (5.27 g, 29.6 mmol) in N,N-dimethylamide (50 mL) was added sodium hydride (1.4 g, 35 mmol) during 5 min at 0° C. After 10 min at 0° C., 6-chloronicotinic acid ethyl ester (5.0 g, 26.9 mmol) was added dropwise and the reaction was heated to 135° C. for 45 min. The mixture was diluted with water (200 mL) and saturated NH4Cl(aq) (100 mL). The formed precipitate was filtrated and washed with water, methanol, ethyl acetate and diethyl ether. The residual green yellow solid was dried to give 4.1 g (47% yield) of the title compound: 1H NMR (DMSO-d6, 300 MHz) δ 14.57 (s, 1 H), 11.24 (s, 1 H), 8.73 (s, 1 H), 8.26 (s, 1 H), 8.10 (d, J=9 Hz, 1 H), 7.92 (d, J=8 Hz, 1 H), 7.67 (d, J=9 Hz, 1 H), 7.03 (d, J=9 Hz, 1 H), 4.31 (q, J=7 Hz, 2 H), 1.32 (t, J=7 Hz, 3 H).

Workup

  1. filtrationThe formed precipitate was filtrated
  2. washwashed with water, methanol, ethyl acetate and diethyl ether
  3. customThe residual green yellow solid was dried

Sources & evidence

ORD record
ord-51f10148c2b244578cb1b35431e2799d
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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