5-Amino-2-methylphenol → HCID 21956454, compound

HRID 2213761Notes

Reaction equation

HRID 2213761 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:3]=12.[NH2:17][C:18]1[CH:23]=[C:22]([OH:24])[C:21]([CH3:25])=[CH:20][CH:19]=1>C(OCCO)C>[OH:24][C:22]1[CH:23]=[C:18]([NH:17][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]3[C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[S:12][C:3]=23)[CH:19]=[CH:20][C:21]=1[CH3:25]

Participants

4

Reactant 2

HCID 178185-Amino-2-methylphenolHCID 10824241HCID 10824241, compound

Product 1

HCID 21956454HCID 21956454, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 300 mg (1.20 mmol) of 4-chlorobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile and 160 mg (1.32 mmol) of 5-amino-o-cresol in 5 mL of 2-ethoxyethanol is heated at reflux temperature for 8 hours, then stirred at room temperature overnight. The reaction mixture is partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo to provide 220 mg (55%) of a light yellow solid, mp 260° C. dec.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 8 hours
  3. customThe reaction mixture is partitioned between ethyl acetate and saturated sodium bicarbonate
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c0a31816c6443058be1e7cf7cae722d
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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