Hydrochloric Acid → 3-Formyl-4-methoxybenzamide

HRID 558436Notes

Reaction equation

HRID 558436 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7](O)=[O:8].[Cl-].[NH4+].O.[N:20]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.Cl>CN(C)C=O>[CH:3]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([NH2:20])=[O:8])=[O:2]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 231414123-Dimethoxymethyl-4-methoxybenzoic acid

Product 1

HCID 231413863-Formyl-4-methoxybenzamideYield 71.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Dimethoxymethyl-4-methoxybenzoic acid (1.81 g) obtained in step B, 0.65 g of ammonium chloride, 1.48 g of benzotriazol-1-ol monohydrate, and 1.85 g of (3-dimethylaminopropyl)ethylcarbodiimide hydrochloride were dissolved in 50 mL of N,N-dimethylformamide, and 4.20 mL of N,N-diisopropylethylamine was added to the solution. The resulting solution was stirred for 13 hours at room temperature, and then 1M hydrochloric acid was added little by little until the mixture reached nearly pH 2. This mixture was extracted with ethyl acetate twice, whereafter the organic layer combined was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The residue was washed with ethanol, and then dried under reduced pressure to obtain 1.03 g (71%) of 3-formyl-4-methoxybenzamide.

Workup

  1. extractionThis mixture was extracted with ethyl acetate twice
  2. washwhereafter the organic layer combined was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. washThe residue was washed with ethanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f5fc2e70d3c540dda3dc88ace760abda
Source dataset
uspto-grants-2011_11
Patent number
US08063046B2

Reaction notes

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