Phthalimide → 4-Amino-5,7-dichloro-2,3-dihydro-2-methylbenzofuran

HRID 1638929Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:9]([Cl:13])=[CH:10][C:11]=1[Cl:12])[NH2:8])[CH:2]=C.[C:14]1(=O)OC(=O)C2=CC=CC=C12.C(OC1C=C(C(F)=CC=1Cl)N)C=C.C1(=O)NC(=O)C2=CC=CC=C12.NC1(F)C2CC(C)OC2=C(Cl)C=C1>>[NH2:8][C:7]1[C:6]2[CH2:14][CH:1]([CH3:2])[O:4][C:5]=2[C:11]([Cl:12])=[CH:10][C:9]=1[Cl:13]

Participants

Reactant 5

HCID 6809Phthalimide

HCID 6811Phthalic Anhydride

HCID 132729265-Allyloxy-4-chloro-2-fluoroaniline

HCID 53865284HCID 53865284, compound

HCID 67926703HCID 67926703, compound

Product 1

HCID 539711784-Amino-5,7-dichloro-2,3-dihydro-2-methylbenzofuran

Procedure

4-amino-5,7-dichloro-2,3-dihydro-2-methylbenzofuran (38A) was prepared as an orange oil in four steps from 3-(allyloxy)-4,6-dichloroaniline and phthalic anhydride by the procedures described for preparing Example 19 from 19A, followed by hydrazinolysis of the phthalimide intermediate as described for the preparation of 37A.

Sources & evidence

ORD record: ord-c6030d24f944435b970866b2e7183d74
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04881967

Reaction notes

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