Ammonium Chloride → HCID 67480657, compound

HRID 2307524Notes

Reaction equation

HRID 2307524 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26](=[O:39])[C:27]2[CH:32]=[C:31]([N+:33]([O-])=O)[CH:30]=[C:29]([N+:36]([O-])=O)[CH:28]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH3:13].[Cl-].[NH4+]>[Zn].CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26](=[O:39])[C:27]2[CH:32]=[C:31]([NH2:33])[CH:30]=[C:29]([NH2:36])[CH:28]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 73703431HCID 73703431, compound

Product 1

HCID 67480657HCID 67480657, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

3.80 g (6.98 mmol) 3,5-dinitrobenzoic acid 6-[3-(3-methoxy-4-butyloxyphenyl)acryloyloxy]hexyl ester and 1.47 g (27.48 mmol) of ammonium chloride were suspended in 75 ml of a mixture consisting of methanol:water 9:1. 9.07 g (0.139 mol) of zinc powder was then added in one portions. The reaction temperature rose to 36° C. The suspension was then heated at 40° C. for 1.5 hours. The reaction suspension was partitioned between dichloromethane and water. The resulting suspension was filtered, the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water. The organic phase was then dried over sodium sulfate, filtered and concentrated by evaporation to yielded 3.47 g (99%) 3,5-diaminobenzoic acid 6-[3-(3-methoxy-4-butyloxyphenyl)acryloyloxy]hexyl ester as yellow oil

Workup

  1. customrose to 36° C
  2. customThe reaction suspension was partitioned between dichloromethane and water
  3. filtrationThe resulting suspension was filtered
  4. washthe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water
  5. dry with materialThe organic phase was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a46c9580942c462caa11e432bc718d76
Source dataset
uspto-grants-2004_12
Patent number
US06831148B2

Reaction notes

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