Hydrochloric Acid → HCID 131730616, compound

HRID 1255385Notes

Reaction equation

HRID 1255385 reaction equation
[C:1]([Cl:4])(=O)[CH3:2].Cl.[NH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[OH:16].C(OC(=O)C)C>C(O)C.C(O)(=O)C.O.CO>[ClH:4].[NH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH2:1][CH3:2])=[O:12])=[CH:9][C:8]=1[OH:16]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 1375664-Amino-3-hydroxybenzoic acid

Product 1

HCID 131730616HCID 131730616, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a dry 100 mL round-bottom flask was added absolute ethanol (50 mL) and the solution cooled to 0° C. (ice-bath) under dry N2(g). Acetyl chloride (5.0 mL) was added slowly with stirring and this solution allowed to stir under anhydrous conditions for 2 hours to prepare anhydrous 1.40 M HCl in ethanol. To this solution was added 4-amino-3-hydroxybenzoic acid (2.50 g, 16.32 mmole) and the mixture allowed to stir as above at room temperature overnight. TLC (irrigant=7:1:1:1 ethylacetate:methanol:water:acetic acid, Rf=0.85) indicated complete conversion to the ethyl ester. Yield 3.5 g (99%).

Workup

  1. stirringto stir under anhydrous conditions for 2 hours
  2. stirringto stir as above at room temperature overnight

Sources & evidence

ORD record
ord-d5dca491f8794736b53bf249f845515a
Source dataset
uspto-grants-2013_06
Patent number
US08460862B2

Reaction notes

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