4-Amino-5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid → 5-Chloro-4-methoxy-2,2-dimethyl-2,3-dihydro-7-benzofurancarboxylic acid

Reaction equation

NC1C2C[C:9](C)(C)[O:10]C=2C(C(OC)=O)=CC=1.N[C:18]1[C:23]2[CH2:24][C:25]([CH3:28])([CH3:27])[O:26][C:22]=2[C:21]([C:29]([OH:31])=[O:30])=[CH:20][C:19]=1[Cl:32]>>[Cl:32][C:19]1[CH:20]=[C:21]([C:29]([OH:31])=[O:30])[C:22]2[O:26][C:25]([CH3:28])([CH3:27])[CH2:24][C:23]=2[C:18]=1[O:10][CH3:9]

Participants

Reactant 2

HCID 106577584-Amino-5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid

HCID 14838335Methyl 4-amino-2,2-dimethyl-2,3-dihydro-7-benzofurancarboxylate

Product 1

HCID 148383345-Chloro-4-methoxy-2,2-dimethyl-2,3-dihydro-7-benzofurancarboxylic acid

Procedure

Following the same procedure, 19.9 g of methyl 4-amino-2,2-dimethyl-2,3-dihydro-7-benzofurancarboxylate was transformed into 20.1 g of 4-amino-5-chloro-2,2-dimethyl-2,3-dihydro-7-benzofurancarboxylic acid, m.p. 176°-178° C.

Sources & evidence

ORD record: ord-6a6f0bc9d2a7491b833efd0f3d327262
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05442078

Reaction notes

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