O-Xylene → HCID 21515664, compound

HRID 593482Notes

Reaction equation

HRID 593482 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[C:11]1([C:17]([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)O)=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(C)C(C)=CC=CC=1>C(Cl)(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:11]1([C:17]2[NH:6][C:5]3[CH:4]=[C:3]4[O:2][CH2:1][O:10][C:9]4=[CH:8][C:7]=3[C:19]=2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 8400BenzoinHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 21515664HCID 21515664, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6212ChloroformSolvent

Procedure

A flask equipped with a Dean-Stark apparatus was charged with 3,4-(methylenedioxy)aniline (5.0 g, 36.4 mmol), p-toluenesulfonic acid (245 mg, 1.2 mmol), benzoin (5.20 g, 24.4 mmol), and xylene (30 mL). The mixture was heated to reflux for 10 hours, then cooled to room temperature. The reaction mixture was diluted with chloroform, then washed twice with 10% sulfuric acid, once with water, and once with brine. The organic layer was concentrated to a minimum volume and petroleum ether was added. The mixture was stirred well and then the precipitated solid was filtered off and dried to give Intermediate 3A (7.0 g, 92%). HPLC: RT=2.261 min (H2O/MeCN with NH4OAc, PUROSPHER® Star RP-18 3 μM, 4×55 mm, gradient=3 min, wavelength=220 nm); MS(ES, negative ionization): m/z=312 [M−H]−.

Workup

  1. customA flask equipped with a Dean-Stark apparatus
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 10 hours
  4. washwashed twice with 10% sulfuric acid, once with water
  5. concentrationThe organic layer was concentrated to a minimum volume and petroleum ether
  6. additionwas added
  7. filtrationthe precipitated solid was filtered off
  8. customdried

Sources & evidence

ORD record
ord-51d158a3580340919906b8a42c1dd283
Source dataset
uspto-grants-2016_01
Patent number
US09242940B2

Reaction notes

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