Sodium Hydroxide → HCID 59828583, compound

HRID 1470614Notes

Reaction equation

C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=O)[C:5]=1[OH:25].[OH-].[Na+]>>[C:16]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[CH:18][C:13]([C:11]2[O:25][C:5]3[C:4]([C:3]([OH:2])=[O:26])=[CH:9][CH:8]=[CH:7][C:6]=3[N:10]=2)=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 56543225HCID 56543225, compound

Product 1

HCID 59828583HCID 59828583, compoundYield 39.6%

Conditions

Temperature: 170 °C

Procedure

3-[(biphenyl-4-carbonyl)-amino]-2-hydroxy-benzoic acid methyl ester (100 mg, 0.28 mmol) was suspended in PPA (500 mg) and heated at 170° C. for 4 h. The reaction was monitored by TLC. After completion of the reaction, the crude mixture was cooled to room temperature and ice water was added. The pH was adjusted to 5 with an aq. solution of 5N NaOH and was extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The crude mixture was purified by column chromatography to get 35 mg of the required product as a pale pink coloured solid.

Workup

customAfter completion of the reaction
extractionwas extracted with ethyl acetate (3×50 mL)
dry with materialThe combined organic phases were dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe crude mixture was purified by column chromatography

Sources & evidence

ORD record: ord-8619799d0d7746c58a823669b040a756
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006454B2

Reaction notes

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