Methanol → HCID 136378428, compound

HRID 1392118Notes

Reaction equation

[OH:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=1)=[CH:8][C:7]([C:26]([O:28]C)=[O:27])=[CH:6][CH:5]=2.CO.[OH-].[Na+]>O>[OH:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=1)=[CH:8][C:7]([C:26]([OH:28])=[O:27])=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of methyl 2-hydroxy-3-[7-(2-methoxyethoxy)quinazolin-4-yl]-1H-indole-5-carboxylate (5.15 g, 13.1 mmol), methanol (100 mL) and water (50 mL) was added aqueous sodium hydroxide (92 mL, 1 M) and the reaction mixture was stirred at 40° C. over night. Methanol was removed in vacuo and the basic aqueous layer was acidified with 1 M hydrochloric acid and stirred for 30 min. The precipitate formed was filtered off, washed with hydrochloric acid (50 mL, 1 M) and water (2×50 mL) and dried in vacuo at 50° C. over night. The crude product was stirred in methanol at room temperature over night. The solid was filtered off to give 4.23 g (85% yield) of the title compound as an orange solid: MS (AP+) m/z 380.3 (M++1).

Workup

customMethanol was removed in vacuo
stirringstirred for 30 min
customThe precipitate formed
filtrationwas filtered off
washwashed with hydrochloric acid (50 mL, 1 M) and water (2×50 mL)
customdried in vacuo at 50° C. over night
stirringThe crude product was stirred in methanol at room temperature over night
filtrationThe solid was filtered off

Sources & evidence

ORD record: ord-394f73905c184a90b4eeee7648ccef9d
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342022B2

Reaction notes

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