Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate → methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylate

HRID 1523715Notes

Reaction equation

HRID 1523715 reaction equation
[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:16][CH2:17][C:18]#[CH:19])[CH:6]=1)(=[O:3])[CH3:2]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.CCCCCC>[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]2[C:6]=1[CH:19]=[CH:18][CH2:17][O:16]2)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 10588933Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

Product 1

HCID 54402287methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylateYield 64.8%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
65 °C

Procedure

A stirred solution of methyl 4-acetylamino-5-chloro-2-(prop-2-ynyloxy)benzoate (25 grams, 88.8 mmol, obtained in above step) in dowtherm A (127 mL) was heated to 220° C. for 3 hours. The reaction mixture was cooled to 60-70° C. and dumped in hexane. The solids precipitated were filtered and washed with hexane to obtain methyl 5-acetylamino-6-chloro-2H-chromene-8-carboxylate (16.2 grams).

Workup

  1. customThe solids precipitated
  2. filtrationwere filtered
  3. washwashed with hexane

Sources & evidence

ORD record
ord-3eabe743580548528b2f958784683d82
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

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