Isopropylamine → 5-Methylbenzofuran

HRID 1283658Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1)C.ClC1C=CC2OC=CC=2C=1.NN.C(N)(C)C>>[CH3:1][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1

Participants

Reactant 4

HCID 6363Isopropylamine

HCID 9321Hydrazine

HCID 900135-Chloro-1-benzofuran

HCID 191050965-Ethylbenzofuran

Product 1

HCID 331035-Methylbenzofuran

Procedure

5-ethylbenzofuran in the procedure of Example 29 for 5-chlorobenzofuran followed by the synthetic steps of hydrazine reduction, acylation, demethylation, epoxide formation and opening of the epoxide with isopropylamine as described therein gives, ultimately, the following substituted benzofurans:

Workup

customas described therein gives

Sources & evidence

ORD record: ord-33ca59347ad94a29a791f4f9bbce4c7d
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03975537

Reaction notes

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