Acetic Acid → HCID 22170312, compound

HRID 1822862Notes

Reaction equation

HRID 1822862 reaction equation
Cl[C:2]1([C:15]([NH2:17])=[O:16])[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]3OCO[C:8]3=[CH:9]2)=[N:4][CH2:3]1.[NH2:18][C:19]1[C:20]([CH3:27])=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][OH:23].C(O)(=O)C>CN(C=O)C.O>[OH:23][CH2:22][C:21]1[C:20]([CH3:27])=[C:19]([CH:26]=[CH:25][CH:24]=1)[NH:18][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:15]([NH2:17])=[O:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 577175(3-Amino-2-methylphenyl)methanolHCID 22170282HCID 22170282, compound

Product 1

HCID 22170312HCID 22170312, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-Chloro-6,7-methylenedioxy-3-quinolinecarboxamide (106 mg, 0.42 mmol); 3-amino-2-methylbenzylalcohol (72 mg, 0.52 mmol) and acetic acid (100 μL) in DMF (2 ml) was heated at 100° C. for 6 h. After cooling, the mixture was diluted with water (20 ml) and washed twice with ethyl acetate. The aqueous phase was made alkaline with 1 M NaOH and the resulting precipitate was collected by filtration, washed with water and dried to give the title compound (113 mg, 75%).

Workup

  1. temperatureAfter cooling
  2. washwashed twice with ethyl acetate
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-58a41fc108ca4bf195d3d84a79a02af6
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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