Ammonia → HCID 67288320, compound

HRID 1626473Notes

Reaction equation

HRID 1626473 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:22])[C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(Cl)(=O)C(Cl)=O.[NH3:34]>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[C:17]([C:16]1[CH:20]=[CH:21][C:13]([O:12][C:11]2[C:10]([Cl:22])=[C:9]3[C:4]([CH:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:6][CH2:7][O:8]3)=[CH:3][C:2]=2[Cl:1])=[CH:14][CH:15]=1)(=[O:18])[NH2:34]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 670803034-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

Product 1

HCID 67288320HCID 67288320, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation A; 150 mg, 0.365 mmol) was diluted with DCM (1.5 mL) followed by the addition of oxalyl chloride in DCM (2M) (201 μl, 0.401 mmol) and DMF (1 drop). Ammonia (6.21 mg, 0.365 mmol) was bubbled in for 10 minutes. The reaction was placed under nitrogen and stirred for 3 hours. The reaction was diluted with ethyl acetate and washed with water. The organic layer was concentrated, loaded onto silica gel and eluted with neat ethyl acetate to yield ethyl 7-(4-carbamoylphenoxy)-6,8-dichlorochroman-4-carboxylate (120 mg, 0.293 mmol, 80.2% yield) as a white solid.

Workup

  1. washwashed with water
  2. concentrationThe organic layer was concentrated
  3. washeluted with neat ethyl acetate

Sources & evidence

ORD record
ord-35d89ae9d4d448f4b129fecb97a5f046
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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