Diazomethane → HCID 14207581, compound

HRID 1252724Notes

Reaction equation

HRID 1252724 reaction equation
[CH2:1]([C:3]1[C:4]2[C:8]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)=[N:7][O:6][CH:5]=2)[CH3:2].[N+](=[CH2:17])=[N-]>CCOCC>[CH2:1]([C:3]1[C:4]2[C:8]([C:9]([CH3:17])=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)=[N:7][O:6][CH:5]=2)[CH3:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 13827101HCID 13827101, compound

Product 1

HCID 14207581HCID 14207581, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-ethyl-6-nitro-anthranil, (1.5 gm, 0.0577 mol.) in anhydrous ether (50 ml) was mixed with an ethereal solution of diazomethane (100 ml, conc. 1 gm CH2N2 /80 ml) and stirred for 16 hrs. The excess diazomethane was removed by pouring the reaction mixture over a short column of silica gel and eluting the column with ether. The ethereal solution was evaporated to give a yellow solid and this solid was purified by column chromatography (40% methylene chloride: pet. ether 30-60) to yield 4-ethyl-7-methyl-6-nitro-anthranil as a solid. The solid was recrystallized from 10% ether: pet ether 30-60, Yield: 1.145 gm. mp. 68°-69° C., IR (CHCl3): 2980, 1625, 1550, 1460 cm-1. H-NMR (CDCl3): 1.40 (t, 3H, CH3), 2.80 (s, 3H, CH3), 2.90 (q, 1H, CH2), 7.30 (br. s, 1H, H5), 9.30 (s, 1H, H3).

Workup

  1. customThe excess diazomethane was removed
  2. additionby pouring the reaction mixture over a short column of silica gel
  3. washeluting the column with ether
  4. customThe ethereal solution was evaporated
  5. customto give a yellow solid
  6. customthis solid was purified by column chromatography (40% methylene chloride: pet. ether 30-60)

Sources & evidence

ORD record
ord-3a9647fed7d04e7d9e9d2313d069b2bf
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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