Allyl bromide → 3-Allyloxycarbonyl-5-nitrobenzoic acid

HRID 1263602

Reaction equation

HRID 1263602 reaction equation
[N+:1]([C:4]1[CH:25]=CC(COC(N2CC(SC(=O)C)CC2C(O)=O)=O)=C[CH:5]=1)([O-])=O.[C:26](=[O:29])([O-])[O-].[K+].[K+].[N+:32]([C:35]1[CH:36]=[C:37]([C:44]([OH:46])=[O:45])[CH:38]=[C:39]([CH:43]=1)[C:40]([OH:42])=[O:41])([O-:34])=[O:33].[CH2:47](Br)[CH:48]=[CH2:49]>CC(N(C)C)=O>[CH2:47]([O:46][C:44](=[O:45])[C:37]1[CH:38]=[C:39]([C:40](=[O:42])[N:1]([O:29][CH3:26])[CH3:4])[CH:43]=[C:35]([NH2:32])[CH:36]=1)[CH:48]=[CH2:49].[CH2:25]([O:45][C:44](=[O:46])[C:37]1[CH:38]=[C:39]([CH:43]=[C:35]([N+:32]([O-:34])=[O:33])[CH:36]=1)[C:40]([OH:42])=[O:41])[CH:4]=[CH2:5]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 120695-Nitroisophthalic acidHCID 135043244-Acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-carboxypyrrolidine

Product 2

HCID 206558603-Allyloxycarbonyl-5-nitrobenzoic acidHCID 229861423-amino-5(N-methyl-methoxycarbamoyl)-benzoic acid allyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Starting material (1(c)) was prepared as described in Example 1. Starting material 7(d) was prepared as follows. A mixture of potassium carbonate (17.00 g), 5-nitro-isophthalic acid (52.00 g), allyl bromide and dimethylacetamide (400 ml) was stirred at 90° for 4 h. Dimethylacetamide was evaporated away under reduced pressure and the residue was dissolved in ethyl acetate, washed with water (2×300 ml) and then extracted with aqueous saturated sodium bicarbonate solution (3×300 ml). The extracts were combined, acidified to pH 4 with concentrated hydrochloric acid and reextracted with ethyl acetate (2×300 ml). The extracts were combined, washed with water (300 ml), dried over magnesium sulphate and evaporated under reduced pressure to give 5-nitro-isophthalic acid 3-allyl ester (7(a)) as a cream solid (39.48 g).

Workup

  1. customwas prepared
  2. customDimethylacetamide was evaporated away under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water (2×300 ml)
  5. extractionextracted with aqueous saturated sodium bicarbonate solution (3×300 ml)
  6. washwashed with water (300 ml)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-14cb1f02fcca437084385a1f8f3df61e
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Linked notes

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