p-Benzyloxypropiophenone → 1H-Indole, 3-methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-

HRID 2427891Notes

Reaction equation

Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16]N)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)=O>C(O)C>[CH2:2]([O:9][C:10]1[CH:15]=[C:14]2[C:13](=[CH:12][CH:11]=1)[NH:16][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=1)=[C:19]2[CH3:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 77.5 °C

Procedure

4-Benzyloxy phenyl hydrazine hydrochloride (1.0 g, 4 mmol), 4-benzyloxy propiophenone (0.96 g, 4 mmol) were suspended in 15 ml of ethanol and mixture was refluxed for 12 hrs at a temperature of 75-80° C. Then the mixture was cooled to 10-15° C. within 1 hr. The white product was filtered and washed with chilled ethanol (3 ml). The title compound 5-benzyloxy-2-(4-benzyloxy phenyl)-3-methyl-1H-indole (formula-1) melting at 152-153° C. and purity by HPLC 99.5% was obtained in a yield of 1.4 g (83.6%).

Workup

temperatureThen the mixture was cooled to 10-15° C. within 1 hr
filtrationThe white product was filtered
washwashed with chilled ethanol (3 ml)

Sources & evidence

ORD record: ord-7637ba9291eb4627a2590556aea70b68
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968732B1

Reaction notes

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