4-((5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid → 6-[(5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinic acid

HRID 1234

Reaction equation

HRID 1234 reaction equation
CC1(C)C2C=C(C#CC3C=CC(C(O)=O)=CC=3)C=CC=2C(=O)CC1.[CH3:25][C:26]1([CH3:50])[C:35]2[CH:34]=[CH:33][C:32]([C:36]#[C:37][C:38]3[CH:48]=[CH:47][C:41]([C:42]([O:44]CC)=[O:43])=[CH:40][N:39]=3)=[CH:31][C:30]=2[C:29](=[O:49])[CH2:28][CH2:27]1>>[CH3:25][C:26]1([CH3:50])[C:35]2[CH:34]=[CH:33][C:32]([C:36]#[C:37][C:38]3[CH:48]=[CH:47][C:41]([C:42]([OH:44])=[O:43])=[CH:40][N:39]=3)=[CH:31][C:30]=2[C:29](=[O:49])[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 153455474-((5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid2×HCID 15391668Ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate2×

Product 1

HCID 183145816-[(5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinic acid

Procedure

Employing the same general procedure as for the preparation of 4-[[5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl]ethynyl]benzoic acid (Compound 7), 300 mg (0.86 mmol) of ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate (Compound 3) was converted into the title compound (pale yellow solid) using 8.6 ml (8.6 mmol) of LiOH (1M aqueous solution).

Sources & evidence

ORD record
ord-4b29fc3fad974c179356548ebb415dfd
Source dataset
uspto-grants-1998_03
Patent number
US05723620

Linked notes

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